N-Tosyloxycarbamates as a source of metal nitrenes: rhodium-catalyzed CH insertion and aziridination reactions

H Lebel, K Huard, S Lectard

Index: Lebel, Helene; Huard, Kim; Lectard, Sylvain Journal of the American Chemical Society, 2005 , vol. 127, # 41 p. 14198 - 14199

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Citation Number: 182

Abstract

The rhodium-catalyzed decomposition of N-tosyloxycarbamates to generate metal nitrenes which undergo intramolecular CH insertion or aziridination reaction is described. Aliphatic N- tosyloxycarbamates produce oxazolidinones with high yields and stereospecificity through insertion in benzylic, tertiary, and secondary CH bonds. Intramolecular aziridination occurs with allylic N-tosyloxycarbamates to produce aziridines as single diastereomers. The ...