Literature DB >> 20681523

Highly diastereoselective Baldwin rearrangement of isoxazolines into cis-acylaziridines.

Eric Gayon1, Olivier Debleds, Marie Nicouleau, Frederic Lamaty, Arie van der Lee, Emmanuel Vrancken, Jean-Marc Campagne.   

Abstract

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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Year:  2010        PMID: 20681523     DOI: 10.1021/jo101273d

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  2 in total

Review 1.  Non-Aziridination Approaches to 3-Arylaziridine-2-carboxylic Acid Derivatives and 3-Aryl-(aziridin-2-yl)ketones.

Authors:  Boriss Strumfs; Kirils Velikijs; Romans Uljanovs; Stanislavs Sinkarevs; Ilze Strumfa
Journal:  Int J Mol Sci       Date:  2022-05-25       Impact factor: 6.208

2.  Gold-catalyzed propargylic substitutions: Scope and synthetic developments.

Authors:  Olivier Debleds; Eric Gayon; Emmanuel Vrancken; Jean-Marc Campagne
Journal:  Beilstein J Org Chem       Date:  2011-06-28       Impact factor: 2.883

  2 in total

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