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The Enantioselective, Brønsted Acid Catalyzed, Vinylogous Mannich Reaction
Author(s) -
Sickert Marcel,
Schneider Christoph
Publication year - 2008
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.200800103
Subject(s) - regioselectivity , phosphoric acid , enantioselective synthesis , mannich reaction , brønsted–lowry acid–base theory , catalysis , chemistry , organic chemistry , silylation , component (thermodynamics) , carboxylic acid , organocatalysis , physics , thermodynamics
Chiral phosphoric acid 4 catalyzes enantioselectively the highly γ‐regioselective addition of a silyl dienolate 2 to imines 1 in good yields and furnishes α,β‐unsaturated δ‐amino carboxylic esters 3 in one step. The reaction may also be carried out as a direct three‐component coupling (PMP= para ‐methoxyphenyl; TBS= tert ‐butyldimethylsilyl).
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