Dual catalysis for the redox annulation of nitroalkynes with indoles: enantioselective construction of indolin-3-ones bearing quaternary stereocenters

Ren-Rong Liu; Shi-Chun Ye; Chuan-Jun Lu; Gui-Lin Zhuang; Jian-Rong Gao; Yi-Xia Jia

doi:10.1002/anie.201504697

Dual catalysis for the redox annulation of nitroalkynes with indoles: enantioselective construction of indolin-3-ones bearing quaternary stereocenters

Angew Chem Int Ed Engl. 2015 Sep 14;54(38):11205-8. doi: 10.1002/anie.201504697. Epub 2015 Aug 5.

Authors

Ren-Rong Liu¹, Shi-Chun Ye¹, Chuan-Jun Lu¹, Gui-Lin Zhuang¹, Jian-Rong Gao¹, Yi-Xia Jia²

Affiliations

¹ College of Chemical Engineering, Zhejiang University of Technology, Chaowang Road 18#, Hangzhou 310014 (China).
² College of Chemical Engineering, Zhejiang University of Technology, Chaowang Road 18#, Hangzhou 310014 (China). [email protected].

PMID: 26245887
DOI: 10.1002/anie.201504697

Abstract

The enantioselective redox annulation of nitroalkynes with indoles is enabled by gold/chiral phosphoric acid dual catalysis. A range of indolin-3-one derivatives bearing quaternary stereocenters at the C2 position were afforded in good yields and excellent enantioselectivities (up to 96 % ee) from readily available starting materials.

Keywords: asymmetric catalysis; carbenoids; chiral phosphoric acids; gold; indolinones.

Publication types

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

MeSH terms

Alkynes / chemistry*
Catalysis
Indoles / chemistry*
Oxidation-Reduction
Stereoisomerism

Substances

Alkynes
Indoles
indoline