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:
rene.wilhelm
tu-clausthal.de
O. Sereda, R. Wilhelm, Synlett, 2007, 3032-3036.
DOI: 10.1055/s-2007-990968
Abstract
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.
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proposed mechanism
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Key Words
catalysis, cycloadditions, lactams, hexamethyldisilazane salts, organocatalysis, Staudinger Synthesis
ID: J60-Y2007-3840
