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Synthesis of Isoxazolidines, Isoxazolines and Isoxazoles from O-Unsaturated Alkoxyamines

[ Vol. 15 , Issue. 5 ]

Author(s):

Julien Escudero, Veronique Bellosta and Janine Cossy*   Pages 365 - 374 ( 10 )

Abstract:


O-Unsaturated alkoxyamines are versatile compounds that can be cyclized to heterocyclic 5-membered rings by using onium ions, transition metals, Brønsted and Lewis acids. O-Allylic and O-homoallylic alkoxyamines can be transformed to isoxazolidines, O-allenyl alkoxyamines to isoxazolidines as well as to 2-isoxazolines and O-alkynyl alkoxyamines to 2- or 3-isoxazolines as well as to isoxazoles.

Keywords:

Alkoxyamine, hydroxylamine, isoxazolidine, isoxazoline, isoxazole, cyclization, synthesis, review.

Affiliation:

Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI), CNRS, ESPCI Paris, PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI), CNRS, ESPCI Paris, PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI), CNRS, ESPCI Paris, PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05

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