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A Way to Highly Enantiomerically Enriched aza‐Morita–Baylis–Hillman–Type Products
Author(s) -
Utsumi Naoto,
Zhang Haile,
Tanaka Fujie,
Barbas Carlos F.
Publication year - 2007
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.200603973
Subject(s) - imidazole , isomerization , chemistry , baylis–hillman reaction , mannich reaction , morita therapy , proline , organic chemistry , stereochemistry , medicinal chemistry , catalysis , amino acid , biochemistry , mathematics , pure mathematics
Going Mannich : Difficult to synthesize β‐amino carbonyl compounds bearing α‐alkylidene groups have been prepared enantioselectively (up to 99 % ee ) by reaction of β‐substituted α,β‐unsaturated aldehydes and α‐imino esters in the presence of ( S )‐proline and imidazole under mild conditions (see scheme, PMP= p ‐methoxyphenyl). Studies suggest that the reaction mechanism involves a Mannich‐type reaction/isomerization sequence.