Enantioselective, Brønsted Acid Catalyzed, Vinylogous Mannich Reaction

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...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2008-04, Vol.47 (19), p.3631-3634
Hauptverfasser: Sickert, Marcel, Schneider, Christoph
Format: Artikel
Sprache:eng
Schlagworte:
asymmetric catalysis
contact ion pairs
CC coupling
organocatalysis
phosphoric acid
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Zusammenfassung: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