碳化物
化学
艾伦
烷基
立体化学
芳基
外消旋化
产量(工程)
催化作用
有机化学
铑
材料科学
冶金
作者
Yang Cao,Paul R. Blakemore
出处
期刊:Synlett
[Georg Thieme Verlag KG]
日期:2023-04-12
卷期号:34 (18): 2200-2204
摘要
Abstract A convenient enantiocontrolled synthesis of allenes (R1R2C=C=CHR3, R1 = aryl/alkyl, R2, R3 = alkyl) is described based on carbenoid eliminative cross-coupling (CEXC) between geometrically pure higher-order α-(methylthio)vinylcuprates, generated in situ by carbocupration of thioalkynes (then activation by addition of n-BuLi), and enantioenriched α-(carbamoyloxy)alkylboronates (15 examples, 30–78% yield, 15–95% ee). The stereochemical fidelity of this CEXC process is substrate dependent, a phenomenon tentatively attributed to a putative organocopper-mediated allene racemization pathway.
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