{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,9]],"date-time":"2026-09-09T16:11:14Z","timestamp":1788970274056,"version":"build-2803163510"},"reference-count":110,"publisher":"American Chemical Society (ACS)","issue":"35","license":[{"start":{"date-parts":[[2026,8,24]],"date-time":"2026-08-24T00:00:00Z","timestamp":1787529600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001692","name":"Croucher Foundation","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001692","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Health@InnoHK Program, Innovation and Technology Commission, Government of HKSAR"},{"name":"Research Grants Council of Hong Kong","award":["24307423"],"award-info":[{"award-number":["24307423"]}]},{"name":"Research Grants Council of Hong Kong","award":["C7001-23Y"],"award-info":[{"award-number":["C7001-23Y"]}]},{"name":"State Key Laboratory of Elemento-organic Chemistry"},{"name":"start-up fund, Chinese University of Hong Kong","award":["4933621"],"award-info":[{"award-number":["4933621"]}]},{"name":"State Key Laboratory of Synthetic Chemistry"},{"name":"Co-funding Mechanism on Joint Laboratories with the Chinese Academy of Sciences (CAS) sponsored by the RGC of HKSAR, China, and the CAS","award":["JLFS\/P-404\/24"],"award-info":[{"award-number":["JLFS\/P-404\/24"]}]},{"name":"National Natural Science Foundation of China\/RGC Joint Research Scheme","award":["N_CUHK452-24"],"award-info":[{"award-number":["N_CUHK452-24"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,9]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Developing new reagents is one efficient strategy for expanding accessible chemical space. Recently, gem-diborylalkanes have emerged as a versatile class of boron-containing reagents with broad reactivity. However, most gem-diborylalkanes are achiral due to the pair of identical boryl groups, which restricts their utility in synthesis, especially for the production of enantioenriched products. To date, only a handful of chiral analogues have been reported, with constricted structural diversity and limited stereospecific transformations. Here, we report the design of a new class of chiral gem-diborylalkane (CDBA) reagents, featuring two boryl groups with chemically distinguishable reactivities, enabling highly selective and stepwise derivatizations. Their versatility is demonstrated through diverse downstream transformations, including the construction of boron stereogenic centers, the synthesis of boron-containing pharmaceuticals, and the preparation of key intermediates for small molecule drugs. These methods offer a powerful platform for the synthesis of enantioenriched alkylboron compounds and hold potential for enhancing synthetic capabilities in drug discovery and development.<\/jats:p>","DOI":"10.1021\/jacs.6c13223","type":"journal-article","created":{"date-parts":[[2026,8,31]],"date-time":"2026-08-31T21:21:56Z","timestamp":1788211316000},"page":"38422-38431","source":"Crossref","is-referenced-by-count":0,"title":["Enantioenriched Alkylboron\nSynthesis Via a Chiral\nDiborylalkane Platform"],"prefix":"10.1021","volume":"148","author":[{"given":"Hongyi","family":"Tao","sequence":"first","affiliation":[{"name":"the Chinese University of Hong Kong , , Shatin, N.T. , ,","place":["Hong Kong SAR, China, 999077"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0196-3469","authenticated-orcid":true,"given":"Zhongxing","family":"Huang","sequence":"additional","affiliation":[{"name":"the University of Hong Kong , , ,","place":["Hong Kong SAR, China, 999077"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0476-0352","authenticated-orcid":true,"given":"Hairong","family":"Lyu","sequence":"additional","affiliation":[{"name":"the Chinese University of Hong Kong , , Shatin, N.T. , ,","place":["Hong Kong SAR, China, 999077"]},{"name":"the Chinese University of Hong Kong , , Shatin, N.T. , ,","place":["Hong Kong SAR, China, 999077"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,24]]},"reference":[{"key":"2026090910094776900_cit1a","doi-asserted-by":"crossref","DOI":"10.1039\/9781847550644","volume-title":"Contemporary\nboron chemistry","author":"Davidson","year":"2000"},{"key":"2026090910094776900_cit1b","doi-asserted-by":"publisher","first-page":"412","DOI":"10.1039\/C3CS60197H","article-title":"Selection\nof boron reagents for Suzuki\u2013Miyaura coupling","volume":"43","author":"Lennox","year":"2014","journal-title":"Chem. Soc. Rev."},{"key":"2026090910094776900_cit1c","doi-asserted-by":"crossref","DOI":"10.1007\/978-3-319-13054-5","volume-title":"Synthesis\nand application of organoboron compounds","author":"Ferna\u0301ndez","year":"2015"},{"key":"2026090910094776900_cit1d","doi-asserted-by":"publisher","first-page":"10018","DOI":"10.1021\/jacs.5b06794","article-title":"Frustrated lewis pairs","volume":"137","author":"Stephan","year":"2015","journal-title":"J. Am.\nChem. Soc."},{"key":"2026090910094776900_cit1e","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202207067","article-title":"The impact of boron\nhybridisation on photocatalytic processes","volume":"61","author":"Marotta","year":"2022","journal-title":"Angew.\nChem., Int. Ed."},{"key":"2026090910094776900_cit1f","doi-asserted-by":"publisher","first-page":"731","DOI":"10.1038\/nchem.2814","article-title":"The versatility\nof boron in biological target engagement","volume":"9","author":"Diaz","year":"2017","journal-title":"Nat.\nChem."},{"key":"2026090910094776900_cit1g","doi-asserted-by":"publisher","first-page":"1275","DOI":"10.4155\/fmc.09.71","article-title":"Therapeutic potential of boron-containing\ncompounds","volume":"1","author":"Baker","year":"2009","journal-title":"Future Med. Chem."},{"key":"2026090910094776900_cit1h","doi-asserted-by":"publisher","first-page":"31","DOI":"10.1016\/j.chempr.2017.05.008","article-title":"Recent developments in organoboron chemistry: old dogs,\nnew tricks","volume":"3","author":"Fyfe","year":"2017","journal-title":"Chem"},{"key":"2026090910094776900_cit1i","doi-asserted-by":"crossref","DOI":"10.1002\/9781119275602","volume-title":"Boron-based\ncompounds: potential and emerging applications in medicine","author":"Hey-Hawkins","year":"2018"},{"key":"2026090910094776900_cit1j","doi-asserted-by":"publisher","first-page":"2441","DOI":"10.1021\/acs.chemrev.3c00663","article-title":"The Rise of Boron-Containing\nCompounds: Advancements in Synthesis, Medicinal Chemistry, and Emerging\nPharmacology","volume":"124","author":"Grams","year":"2024","journal-title":"Chem. Rev."},{"key":"2026090910094776900_cit1k","doi-asserted-by":"publisher","first-page":"2122","DOI":"10.1039\/c1py00123j","article-title":"Boron-containing polymers as versatile building blocks\nfor functional nanostructured materials","volume":"2","author":"Cheng","year":"2011","journal-title":"Polym.\nChem."},{"key":"2026090910094776900_cit1l","doi-asserted-by":"crossref","DOI":"10.5772\/intechopen.78730","article-title":"Recent\nadvances in boron-containing materials","author":"Aydin","year":"2020"},{"key":"2026090910094776900_cit1m","doi-asserted-by":"publisher","first-page":"8800","DOI":"10.1002\/anie.201911108","article-title":"Boron: its role in energy-related\nprocesses and applications","volume":"59","author":"Huang","year":"2020","journal-title":"Angew. Chem., Int.\nEd."},{"key":"2026090910094776900_cit2a","doi-asserted-by":"publisher","first-page":"486","DOI":"10.1021\/ja01463a055","article-title":"Hydroboration as a\nconvenient procedure\nfor the asymmetric synthesis of alcohols of high optical purity","volume":"83","author":"Brown","year":"1961","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit2b","doi-asserted-by":"publisher","first-page":"5551","DOI":"10.1021\/ja00252a056","article-title":"Highly enantioselective\nborane reduction of ketones catalyzed by chiral oxazaborolidines.\nMechanism and synthetic implications","volume":"109","author":"Corey","year":"1987","journal-title":"J. Am.\nChem. Soc."},{"key":"2026090910094776900_cit2c","doi-asserted-by":"publisher","first-page":"763","DOI":"10.1021\/cr00018a007","article-title":"Asymmetric boron-catalyzed reactions","volume":"93","author":"Deloux","year":"1993","journal-title":"Chem. Rev."},{"key":"2026090910094776900_cit2d","doi-asserted-by":"publisher","first-page":"155","DOI":"10.1016\/S0040-4039(97)10474-9","article-title":"Platinum catalysed\ndiboration of terminal alkenes with chiral diborane (4) compounds","volume":"39","author":"Marder","year":"1998","journal-title":"Tetrahedron Lett."},{"key":"2026090910094776900_cit2e","doi-asserted-by":"publisher","first-page":"9475","DOI":"10.1002\/anie.201004525","article-title":"Enantioselective\nHydrogenation with Chiral Frustrated Lewis Pairs","volume":"49","author":"Chen","year":"2010","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090910094776900_cit2f","doi-asserted-by":"publisher","first-page":"11700","DOI":"10.1002\/anie.201701963","article-title":"Asymmetric synthesis of secondary\nand tertiary boronic esters","volume":"56","author":"Collins","year":"2017","journal-title":"Angew. Chem., Int.\nEd."},{"key":"2026090910094776900_cit2g","doi-asserted-by":"publisher","first-page":"191","DOI":"10.1021\/acs.accounts.7b00530","article-title":"Frustrated Lewis Pairs\nCatalyzed Asymmetric Metal-Free Hydrogenations and Hydrosilylations","volume":"51","author":"Meng","year":"2018","journal-title":"Acc. Chem. Res."},{"key":"2026090910094776900_cit2h","doi-asserted-by":"publisher","first-page":"4664","DOI":"10.1002\/anie.201900907","article-title":"Spiro-Bicyclic Bisborane Catalysts\nfor Metal-Free Chemoselective and Enantioselective Hydrogenation of\nQuinolines","volume":"58","author":"Li","year":"2019","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090910094776900_cit2i","doi-asserted-by":"publisher","first-page":"6524","DOI":"10.1039\/c9sc01454c","article-title":"Highly diastereoselective\npreparation of chiral NHC-boranes stereogenic at the boron atom","volume":"10","author":"Aupic","year":"2019","journal-title":"Chem. Sci."},{"key":"2026090910094776900_cit2j","doi-asserted-by":"publisher","first-page":"10337","DOI":"10.1021\/jacs.0c04558","article-title":"Enantioselective reductive coupling of imines templated\nby chiral diboron","volume":"142","author":"Zhou","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit2k","doi-asserted-by":"publisher","first-page":"1056","DOI":"10.1126\/science.adg1322","article-title":"Boryl radical catalysis\nenables asymmetric radical cycloisomerization reactions","volume":"382","author":"Wang","year":"2023","journal-title":"Science"},{"key":"2026090910094776900_cit2l","doi-asserted-by":"publisher","first-page":"6198","DOI":"10.1021\/acscatal.6c00700","article-title":"Asymmetric\nTransition-Metal-Catalyzed Hydrofunctionalization of Alkenylmetalloids\n(B, Si, and Ge)","volume":"16","author":"Bro\u0308samlen","year":"2026","journal-title":"ACS Catal."},{"key":"2026090910094776900_cit3a","doi-asserted-by":"publisher","first-page":"1772","DOI":"10.1021\/ja030542r","article-title":"Synthesis Chiroptical Properties,\nand Solid-State Structure\nDetermination of Two New Chiral Dipyrrin Difluoroboryl Chelates","volume":"126","author":"Gossauer","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit3b","doi-asserted-by":"publisher","first-page":"3790","DOI":"10.1002\/chem.201900350","article-title":"1, 2-Dihydro-1-hydroxy-2, 3, 1-benzodiazaborine Bearing\nan Acridine Moiety as a Circular Dichroism Probe for Determination\nof Absolute Configuration of Mono-Alcohols","volume":"25","author":"Shimo","year":"2019","journal-title":"Chem.-Eur. J."},{"key":"2026090910094776900_cit3c","doi-asserted-by":"publisher","first-page":"7813","DOI":"10.1002\/anie.202001186","article-title":"Azahelicene-Fused BODIPY Analogues Showing Circularly Polarized Luminescence","volume":"59","author":"Maeda","year":"2020","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090910094776900_cit3d","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202522746","article-title":"Dual Circularly\nPolarized Luminescence from Chiral Boron-Embedded Polycyclic Aromatic\nHydrocarbons","volume":"65","author":"Mori","year":"2025","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090910094776900_cit3e","doi-asserted-by":"publisher","first-page":"83","DOI":"10.1038\/s41557-024-01649-z","article-title":"Modular enantioselective assembly of multi-substituted\nboron-stereogenic BODIPYs","volume":"17","author":"Ren","year":"2025","journal-title":"Nat. Chem."},{"key":"2026090910094776900_cit4a","doi-asserted-by":"crossref","DOI":"10.1021\/bk-2001-0783","volume-title":"Organoboranes for\nsyntheses","author":"Ramachandran","year":"2001"},{"key":"2026090910094776900_cit4b","doi-asserted-by":"publisher","first-page":"10294","DOI":"10.1002\/anie.201102717","article-title":"Synthesis and Reactions of N-Heterocyclic\nCarbene Boranes","volume":"50","author":"Curran","year":"2011","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090910094776900_cit4c","doi-asserted-by":"publisher","first-page":"9091","DOI":"10.1021\/acs.chemrev.6b00193","article-title":"Diboron(4)\nCompounds: From Structural Curiosity to Synthetic Workhorse","volume":"116","author":"Neeve","year":"2016","journal-title":"Chem. Rev."},{"key":"2026090910094776900_cit4d","first-page":"1","volume-title":"Recent\ndevelopments and applications of Lewis acidic boron reagents","author":"Lawson","year":"2017"},{"key":"2026090910094776900_cit4e","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202500223","article-title":"Neutral sp2\u2013sp3 Diboranes: Structures, Reactivities, and Applications\nin Organic Synthesis","volume":"28","author":"Liu","year":"2025","journal-title":"Eur. J. Org. Chem."},{"key":"2026090910094776900_cit5a","doi-asserted-by":"publisher","first-page":"890","DOI":"10.1021\/ol203413w","article-title":"Copper(I)-Catalyzed\nBoryl Substitution\nof Unactivated Alkyl Halides","volume":"14","author":"Ito","year":"2012","journal-title":"Org. Lett."},{"key":"2026090910094776900_cit5b","doi-asserted-by":"publisher","first-page":"694","DOI":"10.1039\/C3SC52824C","article-title":"Iridium-catalyzed diborylation of benzylic C\u2013H\nbonds directed by a hydrosilyl group: synthesis of 1,1-benzyldiboronate\nesters","volume":"5","author":"Cho","year":"2014","journal-title":"Chem. Sci."},{"key":"2026090910094776900_cit5c","doi-asserted-by":"publisher","first-page":"434","DOI":"10.1039\/C5QO00426H","article-title":"Synthesis of 1,1-diboronate esters by cobalt-catalyzed sequential\nhydroboration of terminal alkynes","volume":"3","author":"Zuo","year":"2016","journal-title":"Org. Chem.\nFront."},{"key":"2026090910094776900_cit5d","doi-asserted-by":"publisher","first-page":"3418","DOI":"10.1039\/C7OB00654C","article-title":"Transition-metal-free\nsynthesis of 1,1-diboronate esters with a fully substituted benzylic\ncenter via diborylation of lithiated carbamates","volume":"15","author":"Zhao","year":"2017","journal-title":"Org. Biomol. Chem."},{"key":"2026090910094776900_cit5e","doi-asserted-by":"publisher","first-page":"345","DOI":"10.1038\/s41467-017-00363-4","article-title":"Nickel-catalyzed synthesis of 1,1-diborylalkanes from terminal alkenes","volume":"8","author":"Li","year":"2017","journal-title":"Nat. Commun."},{"key":"2026090910094776900_cit5f","doi-asserted-by":"publisher","first-page":"1050","DOI":"10.1039\/C7OB02978K","article-title":"gem-Diborylalkanes:\nrecent advances in their preparation, transformation and application","volume":"16","author":"Nallagonda","year":"2018","journal-title":"Org. Biomol. Chem."},{"key":"2026090910094776900_cit6a","doi-asserted-by":"publisher","first-page":"3834","DOI":"10.1021\/ja01479a024","article-title":"Hydroboration, XI. The Hydroboration\nof Acetylenes\u2500A Convenient Conversion of Internal Acetylenes\ninto cis-Olefins and of Terminal Acetylenes into Aldehydes","volume":"83","author":"Brown","year":"1961","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit6b","doi-asserted-by":"publisher","first-page":"10581","DOI":"10.1021\/ja505455z","article-title":"Simple\naccess to elusive \u03b1-boryl carbanions and their alkylation: an\numpolung construction for organic synthesis","volume":"136","author":"Hong","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit6c","doi-asserted-by":"publisher","first-page":"3163","DOI":"10.1016\/j.tetlet.2014.03.135","article-title":"On the scope of the Pt-catalyzed\nSrebnik diborylation of diazoalkanes. An efficient approach to chiral\ntertiary boronic esters and alcohols via B-stabilized carbanions","volume":"55","author":"Wommack","year":"2014","journal-title":"Tetrahedron Lett."},{"key":"2026090910094776900_cit6d","doi-asserted-by":"publisher","first-page":"976","DOI":"10.1021\/jacs.6b11757","article-title":"Chemoselective Coupling of 1,1-Bis[(pinacolato)boryl]alkanes\nfor the Transition-Metal-Free Borylation of Aryl and Vinyl Halides:\nA Combined Experimental and Theoretical Investigation","volume":"139","author":"Lee","year":"2017","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit6e","doi-asserted-by":"publisher","first-page":"5501","DOI":"10.1002\/anie.201801679","article-title":"Dual Functionalization\nof \u03b1-Monoboryl Carbanions through Deoxygenative Enolization\nwith Carboxylic Acids","volume":"57","author":"Sun","year":"2018","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090910094776900_cit6f","doi-asserted-by":"publisher","first-page":"2429","DOI":"10.1021\/jacs.9b11944","article-title":"Ketone Synthesis from Benzyldiboronates and Esters:\nLeveraging \u03b1-Boryl Carbanions for Carbon\u2013Carbon Bond\nFormation","volume":"142","author":"Lee","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit6g","doi-asserted-by":"publisher","first-page":"4346","DOI":"10.1039\/D1CC01048D","article-title":"Advances in transition metal-free\ndeborylative transformations of gem-diborylalkanes","volume":"57","author":"Jo","year":"2021","journal-title":"Chem. Commun."},{"key":"2026090910094776900_cit7a","doi-asserted-by":"publisher","first-page":"4315","DOI":"10.1016\/S0040-4039(00)76057-6","article-title":"gem-Dimetallic compounds;\nA novel approach to olefins starting from carbonyl compounds and acetylenic\nderivatives","volume":"7","author":"Cainelli","year":"1966","journal-title":"Tetrahedron Lett."},{"key":"2026090910094776900_cit7b","doi-asserted-by":"publisher","first-page":"5608","DOI":"10.1021\/ja00852a062","article-title":"Reaction of aldehydes\nand ketones with a boron-substituted carbanion, bis(ethylenedioxyboryl)methide.\nSimple aldehyde homologation","volume":"97","author":"Matteson","year":"1975","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit7c","doi-asserted-by":"publisher","first-page":"72","DOI":"10.1039\/D0CS00953A","article-title":"Boron-Wittig olefination with gem-bis(boryl)alkanes","volume":"50","author":"Cuenca","year":"2021","journal-title":"Chem. Soc. Rev."},{"key":"2026090910094776900_cit8a","doi-asserted-by":"publisher","first-page":"17918","DOI":"10.1021\/ja510266x","article-title":"Nonracemic allylic boronates through\nenantiotopic-group-selective\ncross-coupling of geminal bis (boronates) and vinyl halides","volume":"136","author":"Potter","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit8b","doi-asserted-by":"publisher","first-page":"6176","DOI":"10.1021\/jacs.5b03477","article-title":"Enantio-and diastereoselective synthesis of 1, 2-hydroxyboronates\nthrough Cu-catalyzed additions of alkylboronates to aldehydes","volume":"137","author":"Joannou","year":"2015","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit8c","doi-asserted-by":"publisher","first-page":"3917","DOI":"10.1021\/acs.accounts.1c00455","article-title":"Catalytic\nChemo- and Enantioselective Transformations of gem-Diborylalkanes\nand (Diborylmethyl)metallic Species","volume":"54","author":"Lee","year":"2021","journal-title":"Acc. Chem.\nRes."},{"key":"2026090910094776900_cit9a","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202315227","article-title":"Diborodichloromethane as Versatile Reagent for Chemodivergent\nSynthesis\nof gem-Diborylalkanes","volume":"63","author":"Fang","year":"2024","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090910094776900_cit9b","doi-asserted-by":"publisher","first-page":"7010","DOI":"10.1021\/acs.orglett.4c02510","article-title":"Diverse Synthesis of (Thio)ethers and (Thio)esters\nUsing Halodiborylmethane as a Transformable C1 Building Block","volume":"26","author":"Hwang","year":"2024","journal-title":"Org. Lett."},{"key":"2026090910094776900_cit10a","doi-asserted-by":"publisher","first-page":"894","DOI":"10.1038\/nchem.1150","article-title":"Enantioselective\npreparation and chemoselective cross-coupling of 1, 1-diboron compounds","volume":"3","author":"Lee","year":"2011","journal-title":"Nat. Chem."},{"key":"2026090910094776900_cit10b","doi-asserted-by":"publisher","first-page":"3989","DOI":"10.1002\/anie.201208610","article-title":"Regio-and enantioselective\ncopper (I)-catalyzed hydroboration of borylalkenes: asymmetric synthesis\nof 1, 1-diborylalkanes","volume":"52","author":"Feng","year":"2013","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090910094776900_cit10c","doi-asserted-by":"publisher","first-page":"3923","DOI":"10.1021\/jacs.9b12214","article-title":"A Boron\nActivating Effect Enables Cobalt-Catalyzed Asymmetric Hydrogenation\nof Sterically Hindered Alkenes","volume":"142","author":"Viereck","year":"2020","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026090910094776900_cit10d","doi-asserted-by":"publisher","first-page":"3524","DOI":"10.1038\/s41467-022-31234-2","article-title":"Enantioselective Cu-catalyzed double hydroboration of alkynes to\naccess chiral gem-diborylalkanes","volume":"13","author":"Jin","year":"2022","journal-title":"Nat. Commun."},{"key":"2026090910094776900_cit11","doi-asserted-by":"publisher","first-page":"11485","DOI":"10.1002\/anie.201705720","article-title":"A Boron Alkylidene\u2013Alkene\nCycloaddition Reaction: Application to the Synthesis of Aphanamal","volume":"56","author":"Liu","year":"2017","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090910094776900_cit12a","doi-asserted-by":"publisher","first-page":"5481","DOI":"10.1039\/C7CC01254C","article-title":"Stereospecific functionalizations\nand transformations of secondary and tertiary boronic esters","volume":"53","author":"Sandford","year":"2017","journal-title":"Chem. Commun."},{"key":"2026090910094776900_cit12b","doi-asserted-by":"publisher","first-page":"8848","DOI":"10.1039\/C5CS00338E","article-title":"Boron-selective\nreactions as powerful tools for modular synthesis of diverse complex\nmolecules","volume":"44","author":"Xu","year":"2015","journal-title":"Chem. Soc. Rev."},{"key":"2026090910094776900_cit13","doi-asserted-by":"publisher","first-page":"9871","DOI":"10.1021\/jacs.3c14766","article-title":"Enantioselective \u03b1-Boryl Carbene Transformations","volume":"146","author":"Huang","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit14a","doi-asserted-by":"publisher","first-page":"3962","DOI":"10.1021\/om010282r","article-title":"Addition Reactions\nof Bis(pinacolato)diborane(4) to Carbonyl Enones and Synthesis of\n(pinacolato)2BCH2B and (pinacolato)2BCH2CH2B by Insertion and Coupling","volume":"20","author":"Abu Ali","year":"2001","journal-title":"Organometallics"},{"key":"2026090910094776900_cit14b","doi-asserted-by":"publisher","first-page":"448","DOI":"10.1021\/ol403338s","article-title":"Formal Carbon\nInsertion of N-Tosylhydrazone into B\u2013B and B\u2013Si Bonds:\ngem-Diborylation and gem-Silylborylation of sp3 Carbon","volume":"16","author":"Li","year":"2014","journal-title":"Org. Lett."},{"key":"2026090910094776900_cit14c","doi-asserted-by":"publisher","first-page":"11694","DOI":"10.1039\/C7CC06302D","article-title":"Facile insertion\nof a cyclic alkyl(amino) carbene carbon into the B\u2013B bond of\ndiboron(4) reagents","volume":"53","author":"Eichhorn","year":"2017","journal-title":"Chem. Commun."},{"key":"2026090910094776900_cit15a","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202312633","article-title":"Stereoselective Unsymmetrical 1,1-Diborylation of Alkynes with a\nNeutral sp2\u2013sp3 Diboron Reagent","volume":"62","author":"Lou","year":"2023","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090910094776900_cit15b","doi-asserted-by":"publisher","first-page":"14915","DOI":"10.1021\/jacs.5c00974","article-title":"Copper-Catalyzed C\u2013B(sp3) Bond Formation\nthrough the Intermediacy of Cu\u2013B(sp3) Complex","volume":"147","author":"Ye","year":"2025","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit15c","doi-asserted-by":"publisher","first-page":"18397","DOI":"10.1021\/jacs.5c02718","article-title":"Copper-Catalyzed Formal Aldehydic\nC\u2013H Borylation Enabled by an sp2\u2013sp3 Diboron Reagent","volume":"147","author":"Lin","year":"2025","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit16a","doi-asserted-by":"publisher","first-page":"7588","DOI":"10.1021\/ja00545a045","article-title":"\u03b1-Chloro boronic\nesters from homologation of boronic esters","volume":"102","author":"Matteson","year":"1980","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit16b","doi-asserted-by":"publisher","first-page":"7491","DOI":"10.1002\/anie.200702146","article-title":"Lithiated\nCarbamates: Chiral Carbenoids for Iterative Homologation of Boranes\nand Boronic Esters","volume":"46","author":"Stymiest","year":"2007","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090910094776900_cit16c","doi-asserted-by":"publisher","first-page":"3068","DOI":"10.1021\/ja068808s","article-title":"Iterative Stereospecific Reagent-Controlled\nHomologation of Pinacol Boronates by Enantioenriched \u03b1-Chloroalkyllithium\nReagents","volume":"129","author":"Blakemore","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit16d","doi-asserted-by":"publisher","first-page":"1490","DOI":"10.1021\/ol200177f","article-title":"Asymmetric Synthesis of Tertiary and Quaternary Allyl-\nand Crotylsilanes via the Borylation of Lithiated Carbamates","volume":"13","author":"Aggarwal","year":"2011","journal-title":"Org. Lett."},{"key":"2026090910094776900_cit16e","doi-asserted-by":"publisher","first-page":"3174","DOI":"10.1021\/ar5002473","article-title":"Lithiation\u2013Borylation Methodology\nand Its Application in Synthesis","volume":"47","author":"Leonori","year":"2014","journal-title":"Acc. Chem.\nRes."},{"key":"2026090910094776900_cit16f","doi-asserted-by":"publisher","first-page":"14663","DOI":"10.1002\/anie.201608406","article-title":"Regio- and Stereoselective Homologation\nof 1,2-Bis(Boronic Esters): Stereocontrolled Synthesis of 1,3-Diols\nand Sch 725674","volume":"55","author":"Fawcett","year":"2016","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090910094776900_cit16g","doi-asserted-by":"publisher","first-page":"2898","DOI":"10.1039\/C6SC05338F","article-title":"Selective uni- and bidirectional\nhomologation of diborylmethane","volume":"8","author":"Blair","year":"2017","journal-title":"Chem. Sci."},{"key":"2026090910094776900_cit16h","doi-asserted-by":"crossref","first-page":"427","DOI":"10.1002\/0471264180.or105.03","article-title":"The Matteson Reaction","volume-title":"Org. React.","author":"Matteson","year":"2021"},{"key":"2026090910094776900_cit16i","doi-asserted-by":"publisher","first-page":"752","DOI":"10.1126\/science.abm0386","article-title":"Enantioselective\ncatalytic 1,2-boronate rearrangements","volume":"374","author":"Sharma","year":"2021","journal-title":"Science"},{"key":"2026090910094776900_cit16j","doi-asserted-by":"publisher","first-page":"1297","DOI":"10.1038\/s44160-025-00836-1","article-title":"Enantioconvergent carbenoid insertion into carbon\u2013boron bonds","volume":"4","author":"Xie","year":"2025","journal-title":"Nat. Synth."},{"key":"2026090910094776900_cit17","doi-asserted-by":"publisher","DOI":"10.1002\/anie.7517492","article-title":"Mild Generation\nof Highly Nucleophilic\nN-Heterocyclic Carbene Boryl Anion From Neutral sp2\u2013sp3 Diboron Reagents and Its Applications in Nucleophilic Borylation","volume":"65","author":"Sun","year":"2026","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090910094776900_cit18","doi-asserted-by":"publisher","first-page":"1424","DOI":"10.1002\/anie.199014241","article-title":"Generation of a Configurationally\nStable Chiral Benzyllithium Derivative, and the Capricious Stereochemistry\nof Its Electrophilic Substitution","volume":"29","author":"Hoppe","year":"1990","journal-title":"Angew. Chem.,\nInt. Ed. Engl."},{"key":"2026090910094776900_cit19a","doi-asserted-by":"publisher","first-page":"1529","DOI":"10.1021\/om50005a008","article-title":"Homologation\nof boronic\nesters to.alpha.-chloro boronic esters","volume":"2","author":"Matteson","year":"1983","journal-title":"Organomet."},{"key":"2026090910094776900_cit19b","doi-asserted-by":"publisher","first-page":"2275","DOI":"10.1055\/s-2004-832835","article-title":"Stereospecific reaction\nof \u03b1-carbamoyloxy-2-alkenylboronates and \u03b1-carbamoyloxy-alkylboronates\nwith Grignard reagents-synthesis of highly enantioenriched secondary\nalcohols","volume":"2004","author":"Beckmann","year":"2004","journal-title":"Synlett"},{"key":"2026090910094776900_cit19c","doi-asserted-by":"publisher","first-page":"12011","DOI":"10.1039\/C6CC05524A","article-title":"Stability and reactivity control of carbenoids: recent\nadvances and perspectives","volume":"52","author":"Gessner","year":"2016","journal-title":"Chem. Commun."},{"key":"2026090910094776900_cit20a","doi-asserted-by":"publisher","first-page":"16856","DOI":"10.1021\/ja307861n","article-title":"Stereospecific\nCross-Coupling of Secondary Organotrifluoroborates: Potassium 1-(Benzyloxy)alkyltrifluoroborates","volume":"134","author":"Molander","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit20b","doi-asserted-by":"publisher","first-page":"420","DOI":"10.1021\/ja511247z","article-title":"Copper(I)-Catalyzed\nEnantioselective Nucleophilic Borylation of Aldehydes: An Efficient\nRoute to Enantiomerically Enriched \u03b1-Alkoxyorganoboronate Esters","volume":"137","author":"Kubota","year":"2015","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit20c","doi-asserted-by":"publisher","first-page":"31","DOI":"10.1002\/ajoc.201500284","article-title":"\u03b1-Hydroxyboronate Esters: Formation and Synthetic\nApplications","volume":"5","author":"Clark","year":"2016","journal-title":"Asian J. Org. Chem."},{"key":"2026090910094776900_cit20d","doi-asserted-by":"publisher","first-page":"20357","DOI":"10.1021\/jacs.4c05924","article-title":"Catalytic Asymmetric Transfer Hydrogenation\nof Acylboronates: BMIDA as the Privileged Directing Group","volume":"146","author":"Meng","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit21a","doi-asserted-by":"publisher","first-page":"1581","DOI":"10.1246\/bcsj.77.1581","article-title":"Transformation of aldehydes into\n(E)-1-alkenylsilanes and (E)-1-alkenylboronic\nesters with a catalytic amount of a chromium salt","volume":"77","author":"Takai","year":"2004","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"2026090910094776900_cit21b","doi-asserted-by":"publisher","first-page":"6716","DOI":"10.1021\/ja0716204","article-title":"Simple and Modular\nStrategy for Small Molecule Synthesis: Iterative Suzuki\u2013Miyaura\nCoupling of B-Protected Haloboronic Acid Building Blocks","volume":"129","author":"Gillis","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit21c","doi-asserted-by":"publisher","first-page":"13770","DOI":"10.1021\/ja205910d","article-title":"Amphoteric \u03b1-Boryl\nAldehydes","volume":"133","author":"He","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit21d","doi-asserted-by":"publisher","first-page":"9926","DOI":"10.1021\/ja304173d","article-title":"Boroalkyl\nGroup Migration Provides a Versatile Entry into \u03b1-Aminoboronic\nAcid Derivatives","volume":"134","author":"He","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit21e","doi-asserted-by":"publisher","first-page":"11092","DOI":"10.1002\/anie.201206501","article-title":"Oxidative Geminal Functionalization of Organoboron\nCompounds","volume":"51","author":"He","year":"2012","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090910094776900_cit22","doi-asserted-by":"publisher","first-page":"18873","DOI":"10.1021\/jacs.4c06526","article-title":"Stereospecific Phosphination\nand\nThioetherification of Organoboronic Esters","volume":"146","author":"Liang","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit23","doi-asserted-by":"publisher","first-page":"1749","DOI":"10.1055\/s-0037-1610172","article-title":"A protocol for direct\nstereospecific amination of primary, secondary, and tertiary alkylboronic\nesters","volume":"29","author":"Edelstein","year":"2018","journal-title":"Synlett"},{"key":"2026090910094776900_cit24","doi-asserted-by":"publisher","first-page":"5016","DOI":"10.1002\/anie.200500402","article-title":"Borinium, Borenium, and Boronium\nIons: Synthesis, Reactivity, and Applications","volume":"44","author":"Piers","year":"2005","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026090910094776900_cit25","doi-asserted-by":"publisher","first-page":"6701","DOI":"10.1021\/om400651p","article-title":"Electrophilic\nC\u2013H Borylation and Related Reactions of B\u2013H Boron Cations","volume":"32","author":"Prokofjevs","year":"2013","journal-title":"Organomet."},{"key":"2026090910094776900_cit26a","doi-asserted-by":"publisher","first-page":"4381","DOI":"10.1039\/D3CS00163F","article-title":"Stereoselective formation\nof boron-stereogenic organoboron derivatives","volume":"52","author":"Abdou-Mohamed","year":"2023","journal-title":"Chem. Soc. Rev."},{"key":"2026090910094776900_cit26b","doi-asserted-by":"publisher","first-page":"2401","DOI":"10.1002\/cjoc.202400130","article-title":"Boron-Stereogenic\nCompounds: Synthetic Developments and Opportunities","volume":"42","author":"Guo","year":"2024","journal-title":"Chin. J. Chem."},{"key":"2026090910094776900_cit27a","doi-asserted-by":"publisher","first-page":"33691","DOI":"10.1021\/jacs.5c09400","article-title":"Stereodivergent\nSynthesis of Enantioenriched Organoboron Compounds with Carbon\/Boron\nDual Stereocenters via Rh(I)\/Cu(I)-Catalyzed Enantioselective Desymmetrization\nof B\u2013H Insertions","volume":"147","author":"Liu","year":"2025","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit27b","doi-asserted-by":"publisher","first-page":"9955","DOI":"10.1038\/s41467-025-64905-x","article-title":"Catalytic asymmetric\nconstructions of nitrogen, boron and carbon continuous stereogenic\ncenters","volume":"16","author":"Zhang","year":"2025","journal-title":"Nat. Commun."},{"key":"2026090910094776900_cit27c","doi-asserted-by":"publisher","first-page":"12166","DOI":"10.1021\/jacs.6c00475","article-title":"Nickel-Catalyzed Boron-Stereogenic\nHydroboration","volume":"148","author":"Fang","year":"2026","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit28","doi-asserted-by":"publisher","first-page":"3212","DOI":"10.1016\/j.chempr.2023.06.019","article-title":"Enriched 10B-diboron reagents\nsynthesis from 10BF3","volume":"9","author":"Chen","year":"2023","journal-title":"Chem"},{"key":"2026090910094776900_cit29a","doi-asserted-by":"publisher","first-page":"71","DOI":"10.14338\/IJPT-22-00002.1","article-title":"A Review of Boron Neutron Capture\nTherapy: Its History and Current Challenges","volume":"9","author":"Jin","year":"2022","journal-title":"Int. J. Part. Ther."},{"key":"2026090910094776900_cit29b","doi-asserted-by":"publisher","first-page":"213139","DOI":"10.1016\/j.ccr.2019.213139","article-title":"Boron agents for neutron capture\ntherapy","volume":"405","author":"Hu","year":"2020","journal-title":"Coord. Chem. Rev."},{"key":"2026090910094776900_cit30","doi-asserted-by":"publisher","first-page":"10902","DOI":"10.1021\/jacs.1c06697","article-title":"Enantioselective\nRh-Catalyzed Hydroboration of Silyl Enol Ethers","volume":"143","author":"Dong","year":"2021","journal-title":"J. Am. Chem. Soc."},{"key":"2026090910094776900_cit31","doi-asserted-by":"publisher","first-page":"6480","DOI":"10.1021\/acs.jmedchem.7b00010","article-title":"Synthetic\nApproaches to the New Drugs Approved During 2015","volume":"60","author":"Flick","year":"2017","journal-title":"J. Med. Chem."},{"key":"2026090910094776900_cit32","doi-asserted-by":"publisher","first-page":"2575","DOI":"10.1002\/ejoc.200400833","article-title":"A Total Synthesis\nof (+)- and (\u2212)-Dihydrokavain\nwith a Sonochemical Blaise Reaction as the Key Step","volume":"2005","author":"Wang","year":"2005","journal-title":"Eur. J. Org. Chem."},{"key":"2026090910094776900_cit33","doi-asserted-by":"publisher","first-page":"172","DOI":"10.1038\/s41929-021-00574-5","article-title":"Palladium-catalysed\nenantioselective diacetoxylation of terminal alkenes","volume":"4","author":"Tian","year":"2021","journal-title":"Nat. Catal."}],"container-title":["Journal of the American\nChemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jacs.6c13223","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/35\/38422\/67392498\/jacs.6c13223.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/35\/38422\/67392498\/jacs.6c13223.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,9]],"date-time":"2026-09-09T15:27:43Z","timestamp":1788967663000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jacsat\/article\/148\/35\/38422\/5328200\/Enantioenriched-Alkylboron-Synthesis-Via-a-Chiral"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,24]]},"references-count":110,"journal-issue":{"issue":"35","published-online":{"date-parts":[[2026,8,24]]},"published-print":{"date-parts":[[2026,9,9]]}},"URL":"https:\/\/doi.org\/10.1021\/jacs.6c13223","relation":{},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,24]]}}}