title: Highly diastereoselective Baldwin rearrangement of isoxazolines into cis-acylaziridines.
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.
authors.affiliation: Institut Charles Gerhardt (ICGM), UMR 5253 CNRS-UM2-UM1-ENSCM, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex 5, France.
authors.forename: Eric
authors.initials: E
authors.lastname: Gayon
authors.forename: Olivier
authors.initials: O
authors.lastname: Debleds
authors.forename: Marie
authors.initials: M
authors.lastname: Nicouleau
authors.forename: Frederic
authors.initials: F
authors.lastname: Lamaty
authors.forename: Arie
authors.initials: A
authors.lastname: van der Lee
authors.forename: Emmanuel
authors.initials: E
authors.lastname: Vrancken
authors.forename: Jean-Marc
authors.initials: JM
authors.lastname: Campagne
mesh_terms: D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D007555:Isoxazoles / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; D007555:Isoxazoles