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Chiral Brønsted Acid‐Catalyzed Enantioselective Friedel–Crafts Reaction of 4,7‐Dihydroindoles with Trifluoromethyl Ketones
Author(s) -
Wang Teng,
Zhang GuangWu,
Teng Yuou,
Nie Jing,
Zheng Yan,
Ma JunAn
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000510
Subject(s) - chemistry , friedel–crafts reaction , enantioselective synthesis , trifluoromethyl , phosphoric acid , moiety , organic chemistry , catalysis , brønsted–lowry acid–base theory , tertiary alcohols , indole test , alcohol , organocatalysis , medicinal chemistry , alkyl
In the presence of chiral phosphoric acid, an enantioselective Friedel–Crafts reaction of 4,7‐dihydroindoles with aromatic trifluoromethyl ketones and ethyl 4,4,4‐trifluoroacetoacetate has been realized. A series of 2‐substituted 4,7‐dihydroindoles with a trifluoromethylated tertiary alcohol moiety were obtained in 45–95% yields with 60–93% ee . Furthermore, 2‐functionalized indole derivatives could be produced through a one‐pot process.