Synthesis of chiral [2,3]-fused indolines through enantioselective dearomatization inverse-electron-demand Diels-Alder reaction/oxidation of indoles with 2-(2-nitrovinyl)-1,4-benzoquinone

Sihan Zhao; Shaobing Cheng; Hui Liu; Jiayan Zhang; Min Liu; Weicheng Yuan; Xiaomei Zhang

doi:10.1039/d0cc00693a

Synthesis of chiral [2,3]-fused indolines through enantioselective dearomatization inverse-electron-demand Diels-Alder reaction/oxidation of indoles with 2-(2-nitrovinyl)-1,4-benzoquinone

Chem Commun (Camb). 2020 Apr 14;56(30):4200-4203. doi: 10.1039/d0cc00693a.

Authors

Sihan Zhao¹, Shaobing Cheng¹, Hui Liu¹, Jiayan Zhang¹, Min Liu¹, Weicheng Yuan², Xiaomei Zhang²

Affiliations

¹ Key Laboratory for Asymmetric Synthesis and Chiraltechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, China. xmzhang@cioc.ac.cn and University of Chinese Academy of Sciences, Beijing, China.
² Key Laboratory for Asymmetric Synthesis and Chiraltechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, China. xmzhang@cioc.ac.cn.

PMID: 32167511
DOI: 10.1039/d0cc00693a

Abstract

Enantioselective dearomatization inverse-electron-demand Diels-Alder reaction/oxidation of indoles with 2-(2-nitrovinyl)-1,4-benzoquinone was realised using a chiral bisoxazoline/zinc complex as a catalyst. This transformation allowed for the synthesis of enantioenriched six-membered [2,3]-fused indolines (up to 99% yield and 88% ee).