Premium
Enantioselective Michael‐Type Friedel–Crafts Reactions of Indoles to Enones Catalyzed by a Chiral Camphor‐Based Brønsted Acid
Author(s) -
Zhou Wei,
Xu LiWen,
Li Lyi,
Yang Lei,
Xia ChunGu
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600646
Subject(s) - friedel–crafts reaction , chemistry , enantioselective synthesis , brønsted–lowry acid–base theory , catalysis , camphor , michael reaction , lewis acids and bases , organocatalysis , organic chemistry , chiral lewis acid , medicinal chemistry
Chiral Brønsted acid, D ‐camphorsulfonic acid, was found to be practical and efficient in the catalysis of the enantioselective Michael‐type Friedel–Crafts reactions of indoles with aromatic enones to afford the corresponding β‐indolyl ketones in excellent yields and moderate enantioselectivities. A surprising synergistic effect was discovered between BmimBr and D ‐CSA which leads to active catalytic systems for the Friedel–Crafts reaction. The efficiency of these systems might result from the catalytic Lewis acid activation of the Brønsted acids. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)