Organic Chemistry Portal



Hexamethyldisilazane Sodium Salt as Highly Active Lewis Base Catalyst for the Staudinger Reaction

Oksana Sereda, René Wilhelm*

*Institut für Organische Chemie, Technische Universität Clausthal, Leibnizstr. 6, 38678 Clausthal-Zellerfeld, Germany, Email:

O. Sereda, R. Wilhelm, Synlett, 2007, 3032-3036.

DOI: 10.1055/s-2007-990968


Hexamethyldisilazane sodium salt (NaHMDS) is a highly active Lewis base catalyst for the Staudinger reaction with disubstituted ketenes and imines. This organocatalyst gave highly substituted β-lactams in nearly quantitative yield in a very short time of five minutes even at temperatures as low as -78°C.

see article for more examples

proposed mechanism

Key Words

catalysis, cycloadditions, lactams, hexamethyldisilazane salts, organocatalysis, Staudinger Synthesis

ID: J60-Y2007-3840