A New Organocatalytic Approach to Substituted Unsaturated Lactams

Margherita      De Rosa; Carmen      Talotta; Annunziata      Soriente

doi:10.2174/157017809788489936

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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Letters in Organic Chemistry

Title: A New Organocatalytic Approach to Substituted Unsaturated Lactams

Volume: 6 Issue: 4

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

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

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.

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De Rosa Margherita, Talotta Carmen and Soriente Annunziata, A New Organocatalytic Approach to Substituted Unsaturated Lactams, Letters in Organic Chemistry 2009; 6 (4) . https://dx.doi.org/10.2174/157017809788489936