NHC-Copper-Catalyzed Asymmetric Dearomative Silylation of Indoles
Yongjia Shi1, Qian Gao1, Senmiao Xu1,2
1State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute, Lanzhou Institute of Chemical Physics , University of Chinese Academy of Sciences, Chinese Academy of Sciences , Lanzhou 73000 , China.
Abstract:
We report an asymmetric dearomative silylation reaction of 3-acylindoles using a chiral NHC-copper(I) complex as catalyst to afford a range of cyclic α-aminosilanes with high regio- and enantioselectivity. Initial mechanistic studies revealed that the observed high diastereoselectivity was attributed to the facile epimerization of the 3-acyl group. We also demonstrated that the product could be used as a versatile precursor for the synthesis of functionalized indolines in high enantiomeric purity.
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