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Highly Enantioselective Friedel–Crafts Reactions of Indoles with Isatins Catalyzed by Chiral Imidodiphosphoric Acids
Author(s) -
Liu Guofeng,
Zhuo Minghua,
An Dong,
Zhang Guangliang,
Qin Xiangshuo,
Gao Jigang,
Fan Yansen,
Zhang Suoqin
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700175
Subject(s) - enantioselective synthesis , friedel–crafts reaction , chemistry , catalysis , brønsted–lowry acid–base theory , organic chemistry , indole test , combinatorial chemistry
A highly enantioselective Friedel–Crafts arylation of indoles with isatins catalyzed by H 8 ‐1,1’‐bi‐2‐naphthol (BINOL) imidodiphosphoric acids is reported here. This reaction proceeds smoothly under mild conditions and afford a range of 3‐hydroxy‐3‐indolyloxindoles with high yields (<92 %) and excellent enantioselectivities (<99 % ee ). To the best of our knowledge, this is the first example in which the highly enantioselective arylation of indoles with isatins has been catalyzed by a Brønsted acid.
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