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Cooperative Coexistence: Effective Interplay of Two Brønsted Acids in the Asymmetric Synthesis of Isoquinuclidines
Author(s) -
Rueping Magnus,
Azap Cengiz
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200603199
Subject(s) - enantioselective synthesis , electrophile , mannich reaction , imine , nucleophile , chemistry , brønsted–lowry acid–base theory , organocatalysis , michael reaction , cyclohexenone , enone , combinatorial chemistry , catalysis , organic chemistry , stereochemistry
A Mannich–aza‐Michael reaction in which both an electrophile and a nucleophile are activated provides a simple, highly enantioselective route to isoquinuclidines ( 1 ) from imines ( 2 ) and cyclohexenone ( 3 ). A feature of the reaction is the interplay of an achiral and a chiral Brønsted acid, which enable the asymmetric reaction process by cooperative activation of the enone and the imine.