Cu(I)-Catalyzed Asymmetric α-Allenylation of Activated Ketimines with 3-Butynoates
Guang‐Yao Ran, Chen Chen, Xing‐Xing Yang, Zhi Gang Zhao, Wei Du, Ying‐Chun Chen
Abstract
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).
Topics & Concepts
ChemistryRegioselectivityIsoquinolineCatalysisTrifluoromethylAmine gas treatingCombinatorial chemistryNucleophileOrganic chemistryMedicinal chemistryAlkylCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsAsymmetric Synthesis and Catalysis