Catalytic Asymmetric Mukaiyama-Mannich Reaction of Cyclic C-Acylimines with Difluoroenoxysilanes: Access to Difluoroalkylated Indolin-3-ones

Jin-Shan Li; Yong-Jie Liu; Guang-Wu Zhang; Jun-An Ma

doi:10.1021/acs.orglett.7b03213

Catalytic Asymmetric Mukaiyama-Mannich Reaction of Cyclic C-Acylimines with Difluoroenoxysilanes: Access to Difluoroalkylated Indolin-3-ones

Org Lett. 2017 Dec 1;19(23):6364-6367. doi: 10.1021/acs.orglett.7b03213. Epub 2017 Nov 21.

Authors

Jin-Shan Li¹, Yong-Jie Liu¹, Guang-Wu Zhang¹, Jun-An Ma¹

Affiliation

¹ Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300072, P. R. China.

PMID: 29160711
DOI: 10.1021/acs.orglett.7b03213

Abstract

A catalytic enantioselective Mukaiyama-Mannich reaction of cyclic C-acylimines with difluoroenoxysilanes is reported. (S)-TRIP enables the enantioselective synthesis of a series of novel difluoroalkylated indolin-3-ones bearing a quaternary stereocenter in up to 97% yield and 98% ee. The synthetic utility of this protocol is highlighted by efficient conversion of the products to the corresponding indolin-3-one derivatives without any erosion of the enantiopurity.

Publication types

Research Support, Non-U.S. Gov't