Highly diastereoselective Baldwin rearrangement of isoxazolines into cis-acylaziridines.

J Org Chem

Institut Charles Gerhardt (ICGM), UMR 5253 CNRS-UM2-UM1-ENSCM, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex 5, France.

Published: September 2010

An atom-economical and practical synthesis of cis-N-benzenesulfonamide acylaziridines through the Baldwin rearrangement of various N-benzenesulfonamide isoxazolines has been reported. A detailed experimental study revealed the beneficial effect of microwaves and pointed out the crucial role of the temperature in the reaction course. Moderate to good yields and excellent cis stereoselectivities were achieved for 13 examples.

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http://dx.doi.org/10.1021/jo101273dDOI Listing

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