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Highly Diastereoselective Baldwin Rearrangement of Isoxazolines into Acylaziridines
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Highly Diastereoselective Baldwin Rearrangement of Isoxazolines into Acylaziridines

Eric Gayon, Olivier Debleds, Marie Nicouleau, Frédéric Lamaty, Arie van Der Lee, Emmanuel Vrancken et Jean-Marc Campagne
Journal of Organic Chemistry, pp.6050-6053
03/08/2010

Résumé

An atom-economical and practical synthesis of cis-N- benzenesulfonamide acylaziridines through the Baldwin rearrangement of various N-benzenesulfonamide isoxa- zolines 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 stereo- selectivities were achieved for 13 examples.

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