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Synthesis 2011(24): 4050-4058  
DOI: 10.1055/s-0031-1289303
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Modified and Highly Useful Protocol for the Brønsted Acid Catalyzed, Enantioselective, Vinylogous Mannich Reaction with Aliphatic Aldimines

Falko Abels, Christoph Schneider*
Institut für Organische Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, Germany
Fax: +341(97)36599; e-Mail: schneider@chemie.uni-leipzig.de;
Further Information

Publication History

Received 18 August 2011
Publication Date:
20 October 2011 (online)

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Abstract

Highly enantioselective as well as diastereoselective catalytic vinylogous Mannich reactions have been accomplished for the first time with aliphatic straight-chain aldimines and O,O-silylketene acetals and furnish valuable synthetic building blocks in high enantiomeric purity.

Key words

vinylogous Mannich reaction - phosphoric acid - organocatalyis - contact ion pair - dienolate - BINOL

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Enantiomeric excess was determined after hydrogenation and lactamization according to the synthesis of 9.