NHC-Copper-Catalyzed Asymmetric Dearomative Silylation of Indoles

Yongjia Shi; Qian Gao; Senmiao Xu

doi:10.1021/acs.joc.8b02308

NHC-Copper-Catalyzed Asymmetric Dearomative Silylation of Indoles

Yongjia Shi, Qian Gao, Senmiao Xu

Research output: Contribution to journal › Article › peer-review

23 Scopus citations

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.

Original language	English
Pages (from-to)	14758-14767
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	83
Issue number	23
DOIs	https://doi.org/10.1021/acs.joc.8b02308
State	Published - 7 Dec 2018
Externally published	Yes

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title = "NHC-Copper-Catalyzed Asymmetric Dearomative Silylation of Indoles",

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.",

author = "Yongjia Shi and Qian Gao and Senmiao Xu",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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AU - Shi, Yongjia

AU - Gao, Qian

AU - Xu, Senmiao

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Y1 - 2018/12/7

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85058147391

U2 - 10.1021/acs.joc.8b02308

DO - 10.1021/acs.joc.8b02308

M3 - 文章

C2 - 30358397

AN - SCOPUS:85058147391

SN - 0022-3263

VL - 83

SP - 14758

EP - 14767

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 23

ER -

NHC-Copper-Catalyzed Asymmetric Dearomative Silylation of Indoles

Abstract

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