Copper-Catalyzed Ring Opening of Benzofurans and an Enantioselective Hydroamination Cascade

Qing-Feng Xu-Xu; Qiang-Qiang Liu; Xiao Zhang; Shu-Li You

doi:10.1002/anie.201809003

Copper-Catalyzed Ring Opening of Benzofurans and an Enantioselective Hydroamination Cascade

Angew Chem Int Ed Engl. 2018 Nov 12;57(46):15204-15208. doi: 10.1002/anie.201809003. Epub 2018 Oct 15.

Authors

Qing-Feng Xu-Xu¹, Qiang-Qiang Liu¹, Xiao Zhang¹, Shu-Li You^{1

2}

Affiliations

¹ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
² Collaborative Innovation Center of, Chemical Science and Engineering, Tianjin, 300072, China.

PMID: 30251383
DOI: 10.1002/anie.201809003

Abstract

A copper(II) acetate/(R)-DTBM-SEGPHOS-catalyzed ring opening of benzofurans and enantioselective hydroamination cascade with dimethoxymethylsilane (DMMS) and hydroxylamine esters is described. Starting from readily available substituted benzofurans, a series of chiral N,N-dibenzylaminophenols, which are of high interest in pharmaceutical chemistry, were obtained with excellent enantioselectivities (up to 66 % yield, 94 % ee).

Keywords: asymmetric catalysis; copper; dearomatization; heterocycles; synthetic methods.

Publication types

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