Cu(I)-Catalyzed Asymmetric α-Allenylation of Activated Ketimines with 3-Butynoates

作者：Guang‐Yao Ran, Chen Chen, Xing‐Xing Yang, Zhi Gang Zhao, Wei Du, Ying‐Chun Chen · 发表于：Organic Letters · 年份：2020 · DOI：10.1021/acs.orglett.0c01534 · 被引用次数：27 · 研究领域：Catalytic Alkyne Reactions、Catalytic C–H Functionalization Methods、Asymmetric Synthesis and Catalysis

An asymmetric α-regioselective allenylation reaction of activated ketimines with 3-butynoates is disclosed under Cu(I) catalysis, probably via the generation of nucleophilic γ-allenylcopper species in the presence of diisopropylethylamine. A broad range of imines, derived from diverse ketones such as isatins, pyrazolediones, isoquinoline-1,3,4-triones, and even trifluoromethyl alkynyl ketones, can be utilized, generally affording the corresponding α-allenyl amine derivatives in high yields (≤97%) with excellent enantioselectivities (≤99% ee).