Enantioselective Friedel–Crafts Alkylation Reactions of 3‑Substituted Indoles with Electron-Deficient Alkenes

Highly enantioselective Friedel–Crafts C2-alkylation reactions of 3-substituted indoles with α,β-unsaturated esters and nitroalkenes were developed using chiral Lewis acids as catalysts, which afforded chiral indole derivatives bearing C2-benzylic stereogenic centers in good to excellent yields (up...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2016-04, Vol.81 (7), p.3023-3030
Main Authors: Weng, Jian-Quan, Fan, Ren-Jie, Deng, Qiao-Man, Liu, Ren-Rong, Gao, Jian-Rong, Jia, Yi-Xia
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Highly enantioselective Friedel–Crafts C2-alkylation reactions of 3-substituted indoles with α,β-unsaturated esters and nitroalkenes were developed using chiral Lewis acids as catalysts, which afforded chiral indole derivatives bearing C2-benzylic stereogenic centers in good to excellent yields (up to 99%) and enantioselectivities (up to 96% ee).
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b00123