{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,17]],"date-time":"2026-10-17T04:34:32Z","timestamp":1792211672272,"version":"4.4.0"},"reference-count":55,"publisher":"American Chemical Society (ACS)","issue":"31","license":[{"start":{"date-parts":[[2026,7,28]],"date-time":"2026-07-28T00:00:00Z","timestamp":1785196800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,7,28]],"date-time":"2026-07-28T00:00:00Z","timestamp":1785196800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,7,28]],"date-time":"2026-07-28T00:00:00Z","timestamp":1785196800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/100014717","name":"Youth Science Fund Project","doi-asserted-by":"publisher","award":["82225041"],"award-info":[{"award-number":["82225041"]}],"id":[{"id":"10.13039\/100014717","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004147","name":"Tsinghua University","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/501100004147","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005089","name":"Natural Science Foundation of Beijing Municipality","doi-asserted-by":"publisher","award":["Z230020"],"award-info":[{"award-number":["Z230020"]}],"id":[{"id":"10.13039\/501100005089","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100012166","name":"National Key Research and Development Program of China","doi-asserted-by":"publisher","award":["2025YFA1309001"],"award-info":[{"award-number":["2025YFA1309001"]}],"id":[{"id":"10.13039\/501100012166","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/na","name":"Beijing Municipal Government","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,12]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The enantioselective construction of C(sp3)-rich architectures from renewable feedstocks remains a formidable challenge in synthetic chemistry, particularly when targeting stereocenters with minimal steric differentiation. While radical chemistry provides access to C(sp3)-rich motifs under mild conditions, catalyst-controlled enantioselective radical\u2013radical coupling for such subtly differentiated aliphatic stereocenters has remained elusive. Here, we disclose a visible-light-mediated, nickel-catalyzed enantioselective deaminative cross-coupling of naturally abundant amino acids with unactivated alkenes via in situ-generated alkylzirconocenes. This operationally simple protocol operates without external photocatalysts or stoichiometric reductants, leveraging the intrinsic photoreactivity of alkylzirconocenes to generate both alkyl radicals and the reducing Cp2Zr(III)Cl species. The method exhibits broad functional group tolerance and delivers a wide array of chiral amides with high efficiency and excellent enantioselectivity (up to 83% yield and 99% ee). Notably, it enables the asymmetric construction of stereogenic centers bearing minimally differentiated alkyl substituents that differ by a methylene unit or heteroatom, directly addressing a long-standing challenge in asymmetric catalysis. Mechanistic investigations support a radical\u2013radical cross-coupling pathway controlled by a chiral nickel catalyst, with Cp2Zr(III)Cl serving as a key reductant to sustain the catalytic cycle. This work establishes alkylzirconocenes as versatile platforms for enantioselective radical transformations and offers a sustainable route to value-added chiral carbonyl compounds from amino acids.<\/jats:p>","DOI":"10.1021\/jacs.6c10406","type":"journal-article","created":{"date-parts":[[2026,8,4]],"date-time":"2026-08-04T13:13:46Z","timestamp":1785849226000},"page":"33662-33670","source":"Crossref","is-referenced-by-count":1,"title":["Enantioselective Deaminative\nCross-Coupling of Amino\nAcid Derivatives with Alkylzirconocenes"],"prefix":"10.1021","volume":"148","author":[{"given":"Yuee","family":"Ke","sequence":"first","affiliation":[{"name":"Tsinghua University , , ,","place":["Beijing, China, 100084"]},{"name":"National Institute of Biological Sciences , 7 Science Park Road, Zhongguancun Life Science Park , ,","place":["Beijing, China, 102206"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Linlin","family":"Fan","sequence":"additional","affiliation":[{"name":"National Institute of Biological Sciences , 7 Science Park Road, Zhongguancun Life Science Park , ,","place":["Beijing, China, 102206"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gen","family":"Li","sequence":"additional","affiliation":[{"name":"National Institute of Biological Sciences , 7 Science Park Road, Zhongguancun Life Science Park , ,","place":["Beijing, China, 102206"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7139-5164","authenticated-orcid":true,"given":"Xiangbing","family":"Qi","sequence":"additional","affiliation":[{"name":"Tsinghua University , , ,","place":["Beijing, China, 100084"]},{"name":"National Institute of Biological Sciences , 7 Science Park Road, Zhongguancun Life Science Park , ,","place":["Beijing, China, 102206"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,7,28]]},"reference":[{"issue":"21","key":"2026081210095954800_cit1","doi-asserted-by":"publisher","first-page":"6752","DOI":"10.1021\/jm901241e","article-title":"Escape from flatland: increasing\nsaturation as an approach to improving clinical success","volume":"52","author":"Lovering","year":"2009","journal-title":"J. Med. Chem."},{"issue":"4","key":"2026081210095954800_cit2","doi-asserted-by":"publisher","first-page":"441","DOI":"10.1039\/c3np70108e","article-title":"sp3-sp3 Coupling\nreactions in the synthesis of natural products and biologically active\nmolecules","volume":"31","author":"Geist","year":"2014","journal-title":"Nat. Prod. Rep."},{"issue":"10","key":"2026081210095954800_cit3","doi-asserted-by":"publisher","first-page":"1839","DOI":"10.1016\/j.drudis.2020.07.017","article-title":"Fsp3: A\nnew parameter for drug-likeness","volume":"25","author":"Wei","year":"2020","journal-title":"Drug Discovery\nToday"},{"issue":"22","key":"2026081210095954800_cit4","doi-asserted-by":"publisher","first-page":"13291","DOI":"10.1021\/acs.jmedchem.0c00829","article-title":"Opportunities\nfor tapping into three-dimensional chemical space through a quaternary\ncarbon","volume":"63","author":"Talele","year":"2020","journal-title":"J. Med. Chem."},{"issue":"3","key":"2026081210095954800_cit5","doi-asserted-by":"publisher","first-page":"1417","DOI":"10.1021\/cr100327p","article-title":"Advances\nin transition metal (Pd,\nNi, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics\nas reaction partners","volume":"111","author":"Jana","year":"2011","journal-title":"Chem. Rev."},{"key":"2026081210095954800_cit6","doi-asserted-by":"publisher","first-page":"1703","DOI":"10.1039\/D5QO01749A","article-title":"Recent advances\nin earth-abundant transition-metal-catalysed asymmetric oxidative\nsp3 -sp3 cross-couplings","volume":"13","author":"He","year":"2026","journal-title":"Org. Chem. Front"},{"issue":"18","key":"2026081210095954800_cit7","doi-asserted-by":"publisher","first-page":"10672","DOI":"10.1021\/acscatal.0c02957","article-title":"Recent developments\nin enantioselective transition metal catalysis featuring attractive\nnoncovalent interactions between ligand and substrate","volume":"10","author":"Fanourakis","year":"2020","journal-title":"ACS Catal"},{"issue":"8","key":"2026081210095954800_cit8","doi-asserted-by":"publisher","first-page":"4184","DOI":"10.1021\/acs.chemrev.4c00869","article-title":"Controlling stereoselectivity\nwith noncovalent interactions in chiral phosphoric acid organocatalysis","volume":"125","author":"Betinol","year":"2025","journal-title":"Chem. Rev."},{"issue":"48","key":"2026081210095954800_cit9","doi-asserted-by":"publisher","first-page":"20678","DOI":"10.1073\/pnas.1006402107","article-title":"Attractive noncovalent\ninteractions in asymmetric catalysis:\nLinks between enzymes and small molecule catalysts","volume":"107","author":"Knowles","year":"2010","journal-title":"PNAS"},{"issue":"7","key":"2026081210095954800_cit10","doi-asserted-by":"publisher","first-page":"517","DOI":"10.1038\/nrd1112","article-title":"Lovastatin\nand beyond: the history of the HMG-CoA reductase inhibitors","volume":"2","author":"Tobert","year":"2003","journal-title":"Nat. Rev. Drug Discovery"},{"issue":"22","key":"2026081210095954800_cit11","doi-asserted-by":"publisher","first-page":"7996","DOI":"10.1021\/ja051072z","article-title":"Enantioselective recognition of carboxylates:\na receptor derived from \u03b1-aminoxy acids functions\nas a chiral shift reagent for carboxylic acids","volume":"127","author":"Yang","year":"2005","journal-title":"J. Am. Chem. Soc."},{"issue":"32","key":"2026081210095954800_cit12","doi-asserted-by":"publisher","first-page":"14856","DOI":"10.1021\/jacs.2c06154","article-title":"Catalytic\nenantioselective \u03b1-alkylation of amides by\nunactivated alkyl electrophiles","volume":"144","author":"Tong","year":"2022","journal-title":"J. Am. Chem.\nSoc."},{"issue":"1","key":"2026081210095954800_cit13","doi-asserted-by":"publisher","first-page":"2938","DOI":"10.1038\/s41467-023-38702-3","article-title":"Ligand-enabled Ni-catalysed\nenantioconvergent intermolecular alkyl-alkyl cross-coupling between\ndistinct alkyl halides","volume":"14","author":"Zhao","year":"2023","journal-title":"Nat. Commun."},{"issue":"13","key":"2026081210095954800_cit14","doi-asserted-by":"publisher","first-page":"4594","DOI":"10.1021\/ja0506509","article-title":"Asymmetric nickel-catalyzed\nNegishi cross-couplings of secondary \u03b1-bromo\namides with organozinc reagents","volume":"127","author":"Fischer","year":"2005","journal-title":"J. Am. Chem.\nSoc."},{"issue":"7731","key":"2026081210095954800_cit15","doi-asserted-by":"publisher","first-page":"379","DOI":"10.1038\/s41586-018-0669-y","article-title":"Catalytic enantioconvergent coupling of secondary and\ntertiary electrophiles with olefins","volume":"563","author":"Wang","year":"2018","journal-title":"Nature"},{"issue":"6","key":"2026081210095954800_cit16","doi-asserted-by":"publisher","first-page":"1754","DOI":"10.1002\/anie.201813222","article-title":"NiH-Catalyzed remote\nasymmetric hydroalkylation of alkenes with racemic \u03b1-bromo amides","volume":"58","author":"Zhou","year":"2019","journal-title":"Angew. Chem., Int. 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Ed."},{"issue":"6","key":"2026081210095954800_cit26","doi-asserted-by":"publisher","first-page":"1832","DOI":"10.1021\/jacs.5b13211","article-title":"Enantioselective\ndecarboxylative arylation of \u03b1-amino acids via the merger of photoredox\nand nickel catalysis","volume":"138","author":"Zuo","year":"2016","journal-title":"J. Am. Chem. Soc."},{"issue":"13","key":"2026081210095954800_cit27","doi-asserted-by":"publisher","first-page":"10999","DOI":"10.1021\/jacs.4c15275","article-title":"Enantioselective alkyl\u2013acyl\nradical cross-coupling enabled by metallaphotoredox catalysis","volume":"147","author":"Li","year":"2025","journal-title":"J. Am. Chem. Soc."},{"issue":"51","key":"2026081210095954800_cit28","doi-asserted-by":"publisher","first-page":"13896","DOI":"10.1002\/ange.201307766","article-title":"Deaminative and\ndecarboxylative catalytic alkylation of amino acids\nwith ketones","volume":"125","author":"Kalutharage","year":"2013","journal-title":"Angew. Chem., Int. Ed."},{"issue":"3","key":"2026081210095954800_cit29","doi-asserted-by":"publisher","first-page":"1130","DOI":"10.1021\/jacs.1c12350","article-title":"Enantioselective deaminative\nalkylation of amino acid derivatives with unactivated olefins","volume":"144","author":"Sun","year":"2022","journal-title":"J. Am. Chem. Soc."},{"issue":"3","key":"2026081210095954800_cit30","doi-asserted-by":"publisher","first-page":"586","DOI":"10.1039\/D2SC05654B","article-title":"Catalytic\nphotochemical enantioselective \u03b1-alkylation\nwith pyridinium salts","volume":"14","author":"Yetra","year":"2023","journal-title":"Chem. Sci."},{"issue":"1","key":"2026081210095954800_cit31","doi-asserted-by":"publisher","first-page":"236","DOI":"10.1021\/acscatal.8b04191","article-title":"Visible-light-mediated\ndeaminative three-component dicarbofunctionalization of styrenes with\nbenzylic radicals","volume":"9","author":"Klauck","year":"2019","journal-title":"ACS Catal"},{"issue":"24","key":"2026081210095954800_cit32","doi-asserted-by":"publisher","first-page":"9264","DOI":"10.1002\/anie.201911660","article-title":"Pyridinium salts as\nredox-active\nfunctional group transfer reagents","volume":"59","author":"Ro\u0308ssler","year":"2020","journal-title":"Angew. Chem.,\nInt. Ed."},{"issue":"4","key":"2026081210095954800_cit33","doi-asserted-by":"publisher","first-page":"503","DOI":"10.1039\/C9CC08348K","article-title":"Photoinduced deaminative strategies: Katritzky salts\nas alkyl radical precursors","volume":"56","author":"Correia","year":"2020","journal-title":"Chem. Commun."},{"issue":"12","key":"2026081210095954800_cit34","doi-asserted-by":"publisher","first-page":"11362","DOI":"10.1021\/acscatal.8b03437","article-title":"Redox-activated amines in C(sp3)\u2013C(sp) and C(sp3)\u2013C(sp2) bond formation enabled by metal-free\nphotoredox catalysis","volume":"8","author":"Ociepa","year":"2018","journal-title":"ACS Catal"},{"issue":"6","key":"2026081210095954800_cit35","doi-asserted-by":"publisher","DOI":"10.1126\/sciadv.aaw9516","article-title":"Ni-catalyzed\ndeaminative cross-electrophile coupling\nof Katritzky salts with halides via C\u2500N bond\nactivation","volume":"5","author":"Ni","year":"2019","journal-title":"Sci. Adv."},{"issue":"8","key":"2026081210095954800_cit36","doi-asserted-by":"publisher","first-page":"2402","DOI":"10.1002\/anie.201813689","article-title":"Deaminative\n(Carbonylative) alkyl-Heck-type reactions enabled by photocatalytic\nC\u2013N bond activation","volume":"58","author":"Jiang","year":"2019","journal-title":"Angew. Chem., Int.\nEd."},{"issue":"21","key":"2026081210095954800_cit37","doi-asserted-by":"publisher","first-page":"5433","DOI":"10.1002\/chem.201900886","article-title":"Photoinduced C(sp3)\u2013N bond cleavage leading to the stereoselective syntheses\nof alkenes","volume":"25","author":"Yang","year":"2019","journal-title":"Chem. Eur. J."},{"issue":"9","key":"2026081210095954800_cit38","doi-asserted-by":"publisher","first-page":"3346","DOI":"10.1021\/acs.orglett.9b01097","article-title":"Deaminative reductive arylation enabled by nickel\/photoredox\ndual catalysis","volume":"21","author":"Yi","year":"2019","journal-title":"Org. Lett."},{"issue":"15","key":"2026081210095954800_cit39","doi-asserted-by":"publisher","first-page":"5313","DOI":"10.1021\/jacs.7b02389","article-title":"Harnessing\nalkyl amines as electrophiles for nickel-catalyzed cross couplings\nvia C\u2013N bond activation","volume":"139","author":"Basch","year":"2017","journal-title":"J. Am. Chem.\nSoc."},{"issue":"23","key":"2026081210095954800_cit40","doi-asserted-by":"publisher","first-page":"3443","DOI":"10.1039\/C8QO01046C","article-title":"Visible-light-mediated allylation of alkyl radicals with allylic\nsulfones via a deaminative strategy","volume":"5","author":"Zhang","year":"2018","journal-title":"Org. Chem.\nFront"},{"issue":"11","key":"2026081210095954800_cit41","doi-asserted-by":"publisher","first-page":"6519","DOI":"10.1021\/acscatal.1c01416","article-title":"Photoinduced nickel-catalyzed deaminative cross-electrophile\ncoupling for C(sp2)\u2013C(sp3) and C(sp3)\u2013C(sp3) bond formation","volume":"11","author":"Yang","year":"2021","journal-title":"ACS Catal"},{"issue":"5","key":"2026081210095954800_cit42","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202214247","article-title":"A photoinduced,\nNickel-catalyzed\nreaction for the stereoselective assembly of C-linked glycosides and\nglycopeptides","volume":"135","author":"Wei","year":"2023","journal-title":"Angew. Chem., Int. Ed."},{"issue":"51","key":"2026081210095954800_cit43","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202312102","article-title":"Visible light induced\ncopper-catalyzed enantioselective\ndeaminative arylation of amino acid derivatives assisted by phenol","volume":"135","author":"Jia","year":"2023","journal-title":"Angew. Chem., Int. Ed."},{"issue":"6","key":"2026081210095954800_cit44","doi-asserted-by":"publisher","first-page":"1061","DOI":"10.1055\/s-0040-1706146","article-title":"Alkylzirconocenes in organic synthesis:\nan overview","volume":"53","author":"Yang","year":"2021","journal-title":"Synthesis"},{"issue":"3","key":"2026081210095954800_cit45","doi-asserted-by":"publisher","first-page":"209","DOI":"10.1038\/nchem.2445","article-title":"Remote functionalization through\nalkene isomerization","volume":"8","author":"Vasseur","year":"2016","journal-title":"Nat. Chem."},{"key":"2026081210095954800_cit46","doi-asserted-by":"publisher","first-page":"348","DOI":"10.1038\/s41929-025-01319-4","article-title":"Photoinduced\nnickel-catalysed enantioconvergent sp3\u2013sp3 coupling of unactivated olefins and aziridines","volume":"8","author":"Zhang","year":"2025","journal-title":"Nat. Catal."},{"issue":"32","key":"2026081210095954800_cit47","doi-asserted-by":"publisher","first-page":"9525","DOI":"10.1021\/ja020236y","article-title":"The electronic influence of ring substituents and ansa\nbridges in zirconocene complexes as probed by infrared spectroscopic,\nelectrochemical, and computational studies","volume":"124","author":"Zachmanoglou","year":"2002","journal-title":"J. Am. Chem. Soc."},{"issue":"3","key":"2026081210095954800_cit48","doi-asserted-by":"publisher","first-page":"675","DOI":"10.1016\/j.chempr.2019.12.010","article-title":"Visible-light-induced\nnickel-catalyzed cross-coupling with alkylzirconocenes from unactivated\nalkenes","volume":"6","author":"Gao","year":"2020","journal-title":"Chem"},{"issue":"26","key":"2026081210095954800_cit49","doi-asserted-by":"publisher","first-page":"11506","DOI":"10.1021\/jacs.0c03821","article-title":"Chemoselective cross-coupling\nof gem-borazirconocene alkanes with aryl halides","volume":"142","author":"Yang","year":"2020","journal-title":"J. Am. Chem. Soc."},{"issue":"8","key":"2026081210095954800_cit50","doi-asserted-by":"publisher","first-page":"2222","DOI":"10.1016\/j.chempr.2023.04.006","article-title":"Visible-light-induced\nenantioselective radical cross-coupling of C(sp3)-borazirconocene","volume":"9","author":"Yang","year":"2023","journal-title":"Chem"},{"issue":"39","key":"2026081210095954800_cit51","doi-asserted-by":"publisher","first-page":"27070","DOI":"10.1021\/jacs.4c09245","article-title":"Enantioselective\ndecarboxylative\nC(sp3)-C(sp3) cross-coupling of aliphatic redox-active\nesters with gem-borazirconocene alkanes","volume":"146","author":"Wang","year":"2024","journal-title":"J. Am. Chem. Soc."},{"issue":"7","key":"2026081210095954800_cit52","doi-asserted-by":"publisher","first-page":"1963","DOI":"10.1016\/j.chempr.2021.06.007","article-title":"Zirconium-redox-shuttled cross-electrophile\ncoupling of aromatic and heteroaromatic halides","volume":"7","author":"Wu","year":"2021","journal-title":"Chem"},{"key":"2026081210095954800_cit53","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.70109","article-title":"Photoinduced EDA complex-enabled\nradical alkylation\/cyclization reaction of N-arylacrylamides with\nKatritzky salts","volume":"367","author":"Li","year":"2025","journal-title":"Adv. Synth. Catal"},{"issue":"10","key":"2026081210095954800_cit54","doi-asserted-by":"publisher","first-page":"3030","DOI":"10.1021\/acs.orglett.8b01062","article-title":"Transforming benzylic amines into\ndiarylmethanes: cross-couplings of benzylic pyridinium salts via C-N\nbond activation","volume":"20","author":"Liao","year":"2018","journal-title":"Org. Lett."},{"issue":"6","key":"2026081210095954800_cit55","doi-asserted-by":"publisher","first-page":"2257","DOI":"10.1021\/jacs.9b00111","article-title":"Harnessing alkylpyridinium\nsalts as electrophiles in deaminative alkyl\u2013alkyl cross-couplings","volume":"141","author":"Plunkett","year":"2019","journal-title":"J. Am. Chem. Soc."}],"container-title":["Journal of the American\nChemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jacs.6c10406","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/31\/33662\/66318615\/jacs.6c10406.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jacsat\/article-pdf\/148\/31\/33662\/66318615\/jacs.6c10406.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,12]],"date-time":"2026-08-12T14:17:26Z","timestamp":1786544246000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jacsat\/article\/148\/31\/33662\/5236090\/Enantioselective-Deaminative-Cross-Coupling-of"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,7,28]]},"references-count":55,"journal-issue":{"issue":"31","published-online":{"date-parts":[[2026,7,28]]},"published-print":{"date-parts":[[2026,8,12]]}},"URL":"https:\/\/doi.org\/10.1021\/jacs.6c10406","relation":{"has-preprint":[{"id-type":"doi","id":"10.26434\/chemrxiv.15001112\/v1","asserted-by":"object"}]},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,7,28]]}}}