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Synthesis 2009(20): 3399-3404  
DOI: 10.1055/s-0029-1216965
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Chemoselective Rearrangement of 3-Aryloxaziridines to Nitrones or Amides

Dong Xing, Xinfang Xu, Liping Yang*
Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R. of China
Fax: +86(21)62232487; e-Mail: lpyang@chem.ecnu.edu.cn;
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Publication History

Received 27 April 2009
Publication Date:
21 August 2009 (online)

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Abstract

An efficient method for the chemoselective ring-opening rearrangement of 3-aryloxaziridines by using silver triflate alone to afford nitrones, or in the presence of a simple Brønsted acid to yield amides, has been developed. Silver triflate plays an important role in both transformations.

Key words

oxaziridines - rearrangement - chemoselectivity - nitrones - amides

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