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