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Enantioselective and Regioselective Friedel–Crafts Alkylation of Pyrroles with Nitroalkenes Catalyzed by a Tridentate Schiff Base–Copper Complex
Author(s) -
Guo Fengfeng,
Chang Dalu,
Lai Guoyin,
Zhu Tao,
Xiong Shunshun,
Wang Sujing,
Wang Zhiyong
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201102206
Subject(s) - regioselectivity , enantioselective synthesis , friedel–crafts reaction , schiff base , catalysis , alkylation , chemistry , combinatorial chemistry , organic chemistry , stereochemistry
On a (pyr)role : A mild and highly efficient catalytic system has been developed for the asymmetric Friedel–Crafts alkylation of pyrroles with nitroalkenes (see scheme). High yields, and excellent enantioselectivities and regioselectivities were obtained for a broad range of substrates. The synthetic utility of this methodology and mechanistic studies involving a novel, negative, nonlinear effect are also presented.