Enantioselective, Brønsted Acid Catalyzed, Vinylogous Mannich Reaction

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‐meth...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2008-04, Vol.47 (19), p.3631-3634
Main Authors: Sickert, Marcel, Schneider, Christoph
Format: Article
Language:English
Subjects:
asymmetric catalysis
contact ion pairs
CC coupling
organocatalysis
phosphoric acid
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200800103