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The Importance of Iminium Geometry Control in Enamine Catalysis: Identification of a New Catalyst Architecture for Aldehyde–Aldehyde Couplings
Author(s) -
Mangion Ian K.,
Northrup Alan B.,
MacMillan David W. C.
Publication year - 2004
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.200461851
Subject(s) - aldol reaction , enamine , aldehyde , iminium , chemistry , catalysis , trifluoroacetic acid , organocatalysis , combinatorial chemistry , organic chemistry , enantioselective synthesis
Central to the design of a new organocatalyst system for aldehyde–aldehyde aldol reactions is the necessity of iminium geometry control during the enamine addition step (see scheme). Significant structural variation in both the aldol donor and aldol acceptor are possible while maintaining high reaction efficiency and enantioselectivity. TFA=trifluoroacetic acid.