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Organocatalytic Asymmetric Cascade Aerobic Oxidation and Semipinacol Rearrangement Reaction: A Visible Light‐Induced Approach to Access Chiral 2,2‐Disubstituted Indolin‐3‐ones
Author(s) -
Bu Liwei,
Li Jiangtao,
Yin Yanli,
Qiao Baokun,
Chai Guobi,
Zhao Xiaowei,
Jiang Zhiyong
Publication year - 2018
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201800446
Subject(s) - enantioselective synthesis , chemistry , yield (engineering) , alkyl , aryl , catalysis , organocatalysis , cascade reaction , cascade , combinatorial chemistry , visible spectrum , stereochemistry , organic chemistry , materials science , optoelectronics , chromatography , metallurgy
An enantioselective cascade aerobic oxidation and semipinacol rearrangement reaction of 2‐aryl‐3‐alkyl‐substituted indoles via visible‐light‐driven cooperative organophotoredox and H‐bonding catalysis is reported. The current method provides an expedient and sustainable approach to furnish a variety of valuable chiral 2‐aryl‐2‐alkyl‐substituted indolin‐3‐ones in 64–90 % yield with 58–94 % ee . Preliminary control experiments present important insights into the stereochemistry.