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