{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,16]],"date-time":"2026-09-16T02:25:02Z","timestamp":1789525502845,"version":"build-2803163510"},"reference-count":85,"publisher":"MDPI AG","issue":"6","license":[{"start":{"date-parts":[[2025,3,7]],"date-time":"2025-03-07T00:00:00Z","timestamp":1741305600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"University of Vienna"},{"name":"University of Turin"},{"name":"All-4-Labels (Hamburg, Germany)"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Modern organic synthesis continues to benefit from the flexibility of \u03b1-diazo carbonyl intermediates. In the context of homologation processes, the Roskamp reaction\u2014first introduced in 1989\u2014has become a valuable tool due to its selectivity and mild condition reactions for accessing important synthons amenable to further functionalization as \u03b2-keto esters. The fine-tuning of reaction parameters\u2014including the nature of Lewis acids, solvents, and temperature\u2014has enabled the development of catalyzed continuous-flow methodologies, as well as a series of asymmetric variants characterized by high transformation rates, excellent stereocontrol, and formidable chemoselectivity. This review aims to emphasize the attractive features of the Roskamp reaction and its applicability for addressing challenging homologation processes.<\/jats:p>","DOI":"10.3390\/molecules30061192","type":"journal-article","created":{"date-parts":[[2025,3,7]],"date-time":"2025-03-07T04:29:59Z","timestamp":1741321799000},"page":"1192","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["The Versatility of the Roskamp Homologation in Synthesis"],"prefix":"10.3390","volume":"30","author":[{"given":"Margherita","family":"Miele","sequence":"first","affiliation":[{"name":"Department of Chemistry, University of Turin, Via P. Giuria 7, 10125 Turin, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aljo\u0161a","family":"Smaji\u0107","sequence":"additional","affiliation":[{"name":"Division of Pharmaceutical Chemistry, Department of Pharmaceutical Sciences, University of Vienna, Josef-Holaubek-Platz 2, A-1090 Vienna, Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3037-5930","authenticated-orcid":false,"given":"Vittorio","family":"Pace","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Turin, Via P. Giuria 7, 10125 Turin, Italy"},{"name":"Division of Pharmaceutical Chemistry, Department of Pharmaceutical Sciences, University of Vienna, Josef-Holaubek-Platz 2, A-1090 Vienna, Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,3,7]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"389","DOI":"10.1007\/s10593-018-2280-4","article-title":"Recent advances in the synthesis and reactivity of spiro-epoxyoxindoles","volume":"54","author":"Monticelli","year":"2018","journal-title":"Chem. Heterocycl. Compd."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"551","DOI":"10.1055\/s-0040-1706404","article-title":"Carbenoid-Mediated Homologation Tactics for Assembling (Fluorinated) Epoxides and Aziridines","volume":"32","author":"Ielo","year":"2021","journal-title":"Synlett"},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Ielo, L., Miele, M., Pillari, V., Castoldi, L., and Pace, V. (2023). Lithium Carbenoids in Homologation Chemistry. Homologation Reactions, Wiley.","DOI":"10.1002\/9783527830237.ch2"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"5761","DOI":"10.1039\/D2CC00886F","article-title":"Straightforward synthesis of bench-stable heteroatom-centered difluoromethylated entities via controlled nucleophilic transfer from activated TMSCHF2","volume":"58","author":"Miele","year":"2022","journal-title":"Chem. Commun."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"623","DOI":"10.1071\/CH21045","article-title":"(Difluoromethyl)trimethylsilane (TMSCHF2): A Useful Difluoromethylating Nucleophilic Source","volume":"74","author":"Miele","year":"2021","journal-title":"Aust. J. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2425","DOI":"10.1039\/D1OB00273B","article-title":"Direct and straightforward transfer of C1 functionalized synthons to phosphorous electrophiles for accessing gem-P-containing methanes","volume":"19","author":"Touqeer","year":"2021","journal-title":"Org. Biomol. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"5444","DOI":"10.1002\/adsc.202000919","article-title":"Consecutive C1-Homologation \/ Displacement Strategy for Converting Thiosulfonates into O,S-Oxothioacetals","volume":"362","author":"Ielo","year":"2020","journal-title":"Adv. Synth. Catal."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"7629","DOI":"10.1021\/acs.orglett.0c02831","article-title":"Chemoselective Homologation\u2013Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes","volume":"22","author":"Miele","year":"2020","journal-title":"Org. Lett."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"288","DOI":"10.1038\/s44160-023-00472-7","article-title":"Homologation reactions for olefin synthesis","volume":"3","author":"Castoldi","year":"2024","journal-title":"Nat. Synth."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"11065","DOI":"10.1039\/D3CC03326K","article-title":"Highly chemoselective homologative assembly of the \u03b1-substituted methylsulfinamide motif from N-sulfinylamines","volume":"59","author":"Malik","year":"2023","journal-title":"Chem. Commun."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1081","DOI":"10.1038\/s41557-018-0139-z","article-title":"Easy as one, two, three","volume":"10","author":"Castoldi","year":"2018","journal-title":"Nat. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2277","DOI":"10.1002\/adsc.202400008","article-title":"Ruppert-Prakash Reagent (TMSCF3)-Catalyzed Chemoselective Esterification of Weinreb Amides","volume":"366","author":"Miele","year":"2024","journal-title":"Adv. Synth. Catal."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Blangetti, M., de la Vega-Hern\u00e1ndez, K., Miele, M., and Pace, V. (2022). Transition-Metal-Free Reactions of Amides by Tetrahedral Intermediates. Amide Bond Activation, Wiley.","DOI":"10.1002\/9783527830251.ch4"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"7584","DOI":"10.1039\/C6CC03532A","article-title":"Highly efficient synthesis of functionalized \u03b1-oxyketones via Weinreb amides homologation with \u03b1-oxygenated organolithiums","volume":"52","author":"Pace","year":"2016","journal-title":"Chem. Commun."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"131220","DOI":"10.1016\/j.tet.2020.131220","article-title":"Straightforward and direct access to \u03b2-seleno- amines and sulfonylamides via the controlled addition of phenylselenomethyllithium (LiCH2SePh) to imines","volume":"76","author":"Senatore","year":"2020","journal-title":"Tetrahedron"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1970","DOI":"10.1039\/C8OB02312C","article-title":"Chemoselective reduction of isothiocyanates to thioformamides mediated by the Schwartz reagent","volume":"17","author":"Senatore","year":"2019","journal-title":"Org. Biomol. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"12960","DOI":"10.1039\/C9CC06929A","article-title":"Highly chemoselective difluoromethylative homologation of iso(thio)cyanates: Expeditious access to unprecedented \u03b1,\u03b1-difluoro(thio)amides","volume":"55","author":"Miele","year":"2019","journal-title":"Chem. Commun."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"e202400619","DOI":"10.1002\/ejoc.202400619","article-title":"Chemoselective Synthesis of Cyanoformamides from Isocyanates and a Highly Reactive Nitrile Anion Reservoir","volume":"27","author":"Miele","year":"2024","journal-title":"Eur. J. Org. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1285","DOI":"10.1007\/s00706-018-2232-9","article-title":"A practical guide for using lithium halocarbenoids in homologation reactions","volume":"149","author":"Monticelli","year":"2018","journal-title":"Monatshefte F\u00fcr Chem.-Chem. Mon."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2937","DOI":"10.1021\/acs.chemrev.5b00381","article-title":"Homologation Reaction of Ketones with Diazo Compounds","volume":"116","author":"Candeias","year":"2016","journal-title":"Chem. Rev."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1091","DOI":"10.1021\/cr00028a010","article-title":"Organic Synthesis with .alpha.-Diazo Carbonyl Compounds","volume":"94","author":"Ye","year":"1994","journal-title":"Chem. Rev."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"8084","DOI":"10.1021\/ja00778a025","article-title":"Condensations of acyldiazomethanes with aldehydes, ketones, and their derivatives","volume":"94","author":"Wenkert","year":"1972","journal-title":"J. Am. Chem. Soc."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"481","DOI":"10.1016\/S0040-4039(01)93538-5","article-title":"The preparation of acylacetylenic derivatives of \u03b1-cyclocitral on route to physiologically active terpenes","volume":"20","author":"Pelicciari","year":"1979","journal-title":"Tetrahedron Lett."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"2732","DOI":"10.1021\/jo00035a036","article-title":"Synthesis of ent-cholesterol, the unnatural enantiomer","volume":"57","author":"Rychnovsky","year":"1992","journal-title":"J. Org. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"4991","DOI":"10.1016\/S0040-4039(00)97786-4","article-title":"The conversion of olefins to \u03b2-keto esters: Ozonolysis of olefins followed by in situ reduction with tin(II) chloride in the presence of ethyl diazoacetate","volume":"31","author":"Holmquist","year":"1990","journal-title":"Tetrahedron Lett."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"3258","DOI":"10.1021\/jo00275a006","article-title":"A selective method for the direct conversion of aldehydes into .beta.-keto esters with ethyl diazoacetate catalyzed by tin(II) chloride","volume":"54","author":"Holmquist","year":"1989","journal-title":"J. Org. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"2460","DOI":"10.1002\/cber.188101402192","article-title":"Condensationen von Ketonen mit Aldehyden","volume":"14","author":"Claisen","year":"1881","journal-title":"Berichte Der Dtsch. Chem. Ges."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1065","DOI":"10.1021\/cr00036a007","article-title":"MASTERING BETA -KETO ESTERS","volume":"95","author":"Benetti","year":"1995","journal-title":"Chem. Rev."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"363","DOI":"10.1016\/j.jare.2014.10.006","article-title":"A mini-review on Biginelli adducts with notable pharmacological properties","volume":"6","author":"Braga","year":"2015","journal-title":"J. Adv. Res."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"9880","DOI":"10.1021\/jo9816515","article-title":"Reaction of Some 1,2-Diaza-1,3-butadienes with Activated Methine Compounds. A Straightforward Entry to 1,4-Dihydropyridazine, Pyridazine, and 4,5(4H,5H)-Cyclopropylpyrazole Derivatives","volume":"63","author":"Attanasi","year":"1998","journal-title":"J. Org. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"377","DOI":"10.1016\/j.petrol.2015.01.019","article-title":"Modeling of fault activation and seismicity by injection directly into a fault zone associated with hydraulic fracturing of shale-gas reservoirs","volume":"127","author":"Rutqvist","year":"2015","journal-title":"J. Pet. Sci. Eng."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"442","DOI":"10.3762\/bjoc.7.57","article-title":"An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals","volume":"7","author":"Baumann","year":"2011","journal-title":"Beilstein J. Org. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"779","DOI":"10.2174\/1871527318666191114092007","article-title":"Structurally Related Edaravone Analogues: Synthesis, Antiradical, Antioxidant, and Copper-Chelating Properties","volume":"18","author":"LeBlanc","year":"2019","journal-title":"CNS Neurol. Disord. Drug Targets"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"154","DOI":"10.1038\/nchembio.746","article-title":"A ketosynthase homolog uses malonyl units to form esters in cervimycin biosynthesis","volume":"8","author":"Bretschneider","year":"2011","journal-title":"Nat. Chem. Biol."},{"key":"ref_35","doi-asserted-by":"crossref","unstructured":"Bingham, S.J., and Tyman, J.H.P. (1997). The synthesis of kermesic acid and isokermesic acid derivatives and of related dihydroxyanthraquinones. J. Chem. Soc.-Perkin Trans. 1, 3637\u20133642.","DOI":"10.1039\/a704317a"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"200","DOI":"10.1002\/cber.19350680142","article-title":"Ein Verfahren zur \u00dcberf\u00fchrung von Carbons\u00e4uren in ihre h\u00f6heren Homologen bzw. deren Derivate","volume":"68","author":"Arndt","year":"1935","journal-title":"Berichte Der Dtsch. Chem. Ges. (A B Ser.)"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"5760","DOI":"10.1021\/jo101105g","article-title":"Improved Arndt- Eistert synthesis of \u03b1-diazoketones requiring minimal diazomethane in the presence of calcium oxide as acid scavenger","volume":"75","author":"Pace","year":"2010","journal-title":"Org. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"4336","DOI":"10.1021\/acs.joc.7b03134","article-title":"\u03b1-Arylamino diazoketones: Diazomethane-loading controlled synthesis, spectroscopic investigations, and structural X-ray analysis","volume":"83","author":"Castoldi","year":"2018","journal-title":"Org. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"2371","DOI":"10.1002\/cber.188501802118","article-title":"Synthese von Ketons\u00e4ure\u00e4thern aus Aldehyden und Diazoessig\u00e4ther","volume":"18","author":"Buchner","year":"1885","journal-title":"Berichte Der Dtsch. Chem. Ges."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"479","DOI":"10.1002\/cber.19070400179","article-title":"Umwandlung von Aldehyden in Ketone durch Diazomethan","volume":"40","author":"Schlotterbeck","year":"1907","journal-title":"Berichte Der Dtsch. Chem. Ges."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1295","DOI":"10.1007\/BF01526540","article-title":"\u00dcber die Einwirkung von Diazomethan auf Aldehyds\u00e4uren und Aldehyde","volume":"26","author":"Meyer","year":"1905","journal-title":"Monatshefte F\u00fcr Chem. Und Verwandte Teile Anderer Wiss."},{"key":"ref_42","unstructured":"Smith, P.A.S., and Baer, D.R. (1960). The Demjanov and Tiffeneau-Demjanov Ring Expansions. Organic Reactions, Wiley."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"2011","DOI":"10.1007\/s00706-019-02514-3","article-title":"The synthetic versatility of the Tiffeneau\u2013Demjanov chemistry in homologation tactics","volume":"150","author":"Kohlbacher","year":"2019","journal-title":"Monatsh. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"14834","DOI":"10.1021\/acs.joc.8b02715","article-title":"One-Pot Reaction of Carboxylic Acids and Ynol Ethers for The Synthesis of \u03b2-Keto Esters","volume":"83","author":"Zeng","year":"2018","journal-title":"J. Org. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"8532","DOI":"10.1021\/ja102832f","article-title":"Catalytic Asymmetric Roskamp Reaction of \u03b1-Alkyl-\u03b1-diazoesters with Aromatic Aldehydes: Highly Enantioselective Synthesis of \u03b1-Alkyl-\u03b2-keto Esters","volume":"132","author":"Li","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1685","DOI":"10.1055\/s-2008-1067029","article-title":"Molybdenum(VI) Dichloride Dioxide Catalyzed Synthesis of \u03b2-Keto Esters by C-H Insertion of Ethyl Diazoacetate into Aldehydes","volume":"2008","author":"Jeyakumar","year":"2008","journal-title":"Synthesis"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"788","DOI":"10.1080\/00397911.2017.1285936","article-title":"Facile synthesis of naturally occurring nor-lignans (\u00b1)-Machicendiol and its analogs","volume":"47","author":"More","year":"2017","journal-title":"Synth. Commun."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"4193","DOI":"10.1039\/b609604b","article-title":"Approaches to the quaternary stereocentre and to the heterocyclic core in diazonamide A using the Heck reaction and related coupling reactions","volume":"4","author":"Booker","year":"2006","journal-title":"Org. Biomol. Chem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"6138","DOI":"10.1021\/acs.joc.0c02972","article-title":"Synthetic Scope of Br\u00f8nsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate","volume":"86","author":"Rahaman","year":"2021","journal-title":"J. Org. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"13237","DOI":"10.1016\/S0040-4020(98)00804-7","article-title":"Simple and high yielding syntheses of \u03b2-keto esters catalysed by zeolites","volume":"54","author":"Balaji","year":"1998","journal-title":"Tetrahedron"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"247","DOI":"10.1039\/b104116a","article-title":"Montmorillonite K-10 catalyzed synthesis of \u03b2-keto esters: Condensation of ethyl diazoacetate with aldehydes under mild conditions","volume":"3","author":"Bandgar","year":"2001","journal-title":"Green Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1117","DOI":"10.1081\/SCC-120028644","article-title":"Synthesis of \u03b2-Keto Esters Promoted by Yttria-Zirconia Based Lewis Acid Catalyst","volume":"34","author":"Pandey","year":"2004","journal-title":"Synth. Commun."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"4788","DOI":"10.1016\/j.tetlet.2008.05.077","article-title":"Selective synthesis of \u03b1-substituted \u03b2-keto esters from aldehydes and diazoesters on mesoporous silica catalysts","volume":"49","author":"Murata","year":"2008","journal-title":"Tetrahedron Lett."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"3525","DOI":"10.1016\/j.tetlet.2014.04.087","article-title":"One pot direct synthesis of \u03b2-ketoesters via carbonylation of aryl halides using cobalt carbonyl","volume":"55","author":"Baburajan","year":"2014","journal-title":"Tetrahedron Lett."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"153296","DOI":"10.1016\/j.tetlet.2021.153296","article-title":"Palladium catalysed hydrolysis-free arylation of aliphatic nitriles for the synthesis of 4-arylquinolin-2-one\/pyrazolone derivatives","volume":"79","year":"2021","journal-title":"Tetrahedron Lett."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"3389","DOI":"10.1002\/adsc.202200602","article-title":"Continuous-Flow Synthesis of \u03b2-Ketoesters and Successive Reactions in One-Flow using Heterogeneous Catalysis","volume":"364","author":"Kandasamy","year":"2022","journal-title":"Adv. Synth. Catal."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"7786","DOI":"10.1002\/anie.201202455","article-title":"Asymmetric synthesis and biosynthetic implications of (+)-fusarisetin\u2005A","volume":"51","author":"Yin","year":"2012","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"3330","DOI":"10.1016\/j.tetlet.2015.01.109","article-title":"Synthetic Studies to Lyngbouilloside: A Phosphate Tether-Mediated Synthesis of the Macrolactone Core","volume":"56","author":"Chegondi","year":"2015","journal-title":"Tetrahedron Lett."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"401","DOI":"10.1002\/ijch.202100019","article-title":"Synthesis of the C1\u2212C16 Polyol-Containing Macrolactone of 13-Desmethyl Lyngbouilloside, an Unnatural Analog of the Originally Assigned Structure of (\u2212)-Lyngbouilloside","volume":"61","author":"Ganguly","year":"2021","journal-title":"Isr. J. Chem."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"11280","DOI":"10.1021\/ja903500w","article-title":"Stereoselective Synthesis of \u03b1-Alkyl-\u03b2-keto Imides via Asymmetric Redox C\u2212C Bond Formation between \u03b1-Alkyl-\u03b1-diazocarbonyl Compounds and Aldehydes","volume":"131","author":"Hashimoto","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"8322","DOI":"10.1002\/anie.201204350","article-title":"Enantioselective Synthesis of \u03b1-Alkyl-\u03b2-ketoesters: Asymmetric Roskamp Reaction Catalyzed by an Oxazaborolidinium Ion","volume":"51","author":"Gao","year":"2012","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"2100","DOI":"10.1002\/anie.200805374","article-title":"Enantioselective Catalysis Based on Cationic Oxazaborolidines","volume":"48","author":"Corey","year":"2009","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"20708","DOI":"10.1021\/ja209270e","article-title":"Oxazaborolidinium Ion-Catalyzed Cyclopropanation of \u03b1-Substituted Acroleins: Enantioselective Synthesis of Cyclopropanes Bearing Two Chiral Quaternary Centers","volume":"133","author":"Gao","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"4398","DOI":"10.1002\/anie.200900351","article-title":"Enantioselective synthesis of beta-iodo Morita-Baylis-Hillman esters by a catalytic asymmetric three-component coupling reaction","volume":"48","author":"Senapati","year":"2009","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"5384","DOI":"10.1021\/ja050543e","article-title":"Enantioselective Cyanosilylation of Ketones Catalyzed by a Chiral Oxazaborolidinium Ion","volume":"127","author":"Ryu","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"2792","DOI":"10.1055\/s-0037-1611549","article-title":"Weinreb Amides as Privileged Acylating Agents for Accessing \u03b1-Substituted Ketones","volume":"51","author":"Senatore","year":"2019","journal-title":"Synthesis"},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"1180","DOI":"10.1039\/D4CC05937A","article-title":"Chemoselective homologative preparation of trisubstituted alkenyl halides from carbonyls and carbenoids","volume":"61","author":"Miele","year":"2025","journal-title":"Chem. Commun."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"8261","DOI":"10.1021\/acs.orglett.9b03024","article-title":"Direct and Chemoselective Synthesis of Tertiary Difluoroketones via Weinreb Amide Homologation with a CHF2-Carbene Equivalent","volume":"21","author":"Miele","year":"2019","journal-title":"Org. Lett."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"1147","DOI":"10.1002\/cssc.201802815","article-title":"Sustainable Asymmetric Organolithium Chemistry: Enantio- and Chemoselective Acylations through Recycling of Solvent, Sparteine, and Weinreb \u201cAmine\u201d","volume":"12","author":"Monticelli","year":"2019","journal-title":"ChemSusChem"},{"key":"ref_70","doi-asserted-by":"crossref","unstructured":"Miele, M., Pillari, V., Pace, V., Alc\u00e1ntara, A.R., and de Gonzalo, G. (2022). Application of biobased solvents in asymmetric catalysis. Molecules, 27.","DOI":"10.3390\/molecules27196701"},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"4746","DOI":"10.1021\/acs.orglett.5b02268","article-title":"Enantioselective Synthesis of syn-\u03b1-Aryl-\u03b2-hydroxy Weinreb Amides: Catalytic Asymmetric Roskamp Reaction of \u03b1-Aryl Diazo Weinreb Amides","volume":"17","author":"Shin","year":"2015","journal-title":"Org. Lett."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"10737","DOI":"10.1021\/jo051747g","article-title":"Asymmetric Intermolecular C\u2212H Functionalization of Benzyl Silyl Ethers Mediated by Chiral Auxiliary-Based Aryldiazoacetates and Chiral Dirhodium Catalysts","volume":"70","author":"Davies","year":"2005","journal-title":"J. Org. Chem."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"848","DOI":"10.1002\/adsc.201100122","article-title":"Organocatalytic Stereoselective Direct Aldol Reaction of Trifluoroethyl Thioesters","volume":"353","author":"Rossi","year":"2011","journal-title":"Adv. Synth. Catal."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"6774","DOI":"10.1021\/ja401731d","article-title":"Sequential C\u2013H Functionalization Reactions for the Enantioselective Synthesis of Highly Functionalized 2,3-Dihydrobenzofurans","volume":"135","author":"Wang","year":"2013","journal-title":"J. Am. Chem. Soc."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"5936","DOI":"10.1021\/acs.orglett.7b02928","article-title":"Catalytic Asymmetric Roskamp Reaction of Silyl Diazoalkane: Synthesis of Enantioenriched \u03b1-Silyl Ketone","volume":"19","author":"Kim","year":"2017","journal-title":"Org. Lett."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"6294","DOI":"10.1002\/anie.201612235","article-title":"Batch and Continuous-Flow One-Pot Processes using Amine Diazotization to Produce Silylated Diazo Reagents","volume":"56","author":"Audubert","year":"2017","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"602","DOI":"10.1021\/ja00107a003","article-title":".alpha.-Silyl Effects on the Acidities of Carbon Acids and the Homolytic Bond Dissociation Enthalpies of Their Acidic C-H Bonds","volume":"117","author":"Zhang","year":"1995","journal-title":"J. Am. Chem. Soc."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"551","DOI":"10.1016\/S1359-6446(03)02726-0","article-title":"Chemistry challenges in lead optimization: Silicon isosteres in drug discovery","volume":"8","author":"Showell","year":"2003","journal-title":"Drug Discov. Today"},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"12360","DOI":"10.1021\/ja971916h","article-title":"Total Synthesis of Filipin III","volume":"119","author":"Richardson","year":"1997","journal-title":"J. Am. Chem. Soc."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"8129","DOI":"10.1021\/jo035054g","article-title":"A Formal Total Synthesis of the Salicylihalamides","volume":"68","author":"Herb","year":"2003","journal-title":"J. Org. Chem."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"1048","DOI":"10.1021\/ja0684996","article-title":"Total Synthesis of (+)-Galbulimima Alkaloid 13 and (+)-Himgaline","volume":"129","author":"Evans","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"925","DOI":"10.1021\/np010526c","article-title":"Lyngbouilloside, a Novel Glycosidic Macrolide from the Marine Cyanobacterium Lyngbya bouillonii","volume":"65","author":"Tan","year":"2002","journal-title":"J. Nat. Prod."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"314","DOI":"10.1021\/ol203064r","article-title":"Total Synthesis of Nominal Lyngbouilloside Aglycon","volume":"14","author":"ElMarrouni","year":"2012","journal-title":"Org. Lett."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"3149","DOI":"10.1039\/C3RA44354J","article-title":"Stereoselective synthesis of the C1\u2013C8 and C9\u2013C16 fragments of revised structure of (\u2212)-lyngbouilloside","volume":"4","author":"Sabitha","year":"2014","journal-title":"RSC Adv."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"868","DOI":"10.1002\/anie.201409629","article-title":"Total Synthesis, Stereochemical Reassignment, and Biological Evaluation of (\u2212)-Lyngbyaloside\u2005B","volume":"54","author":"Fuwa","year":"2015","journal-title":"Angew. Chem. Int. 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