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  • Title: NHC-Copper-Catalyzed Asymmetric Dearomative Silylation of Indoles.
    Author: Shi Y, Gao Q, Xu S.
    Journal: J Org Chem; 2018 Dec 07; 83(23):14758-14767. PubMed ID: 30358397.
    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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