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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

A New Organocatalytic Approach to Substituted Unsaturated Lactams

Author(s): Margherita De Rosa, Carmen Talotta and Annunziata Soriente

Volume 6, Issue 4, 2009

Page: [301 - 305] Pages: 5

DOI: 10.2174/157017809788489936

Price: $65

Abstract

The first organocatalytic approach to erythro and threo lactam derivatives was successfully achieved from the addition of TBSOP (1) to aromatic and aliphatic aldehydes in the presence of a commercially available urea-derivative 5 supporting the broad potential for hydrogen-bond catalysis in the vinylogous Mukaiyama aldol addition. The transition states leading to the major diastereoisomers are discussed.

Keywords: Organocatalysis, TBSOP, Urea-type catalyst, Aldehydes addition, Solvent-free, Vinylogous addition


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