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Paper | Regular issue | Vol 92, No. 11, 2016, pp.1963-1975
Published online, 17th October, 2016
DOI: 10.3987/COM-16-13532
Synthesis of Some Isoxazolidine and Isoxazoline Derivatives Using Nitrone-Derived (‒)-Menthone via 1,3-Dipolar Cycloaddition with Alkenes, Alkynes and Cycloalkenes

Heithem Abda, Kaïss Aouadi,* Moncef Mssadek, and Sébastien Vidal*

*Department of Chemistry, Faculté des Sciences de Monastir, Av de l'environnement 5019, Tunisia

Abstract

Cycloaddition reactions between a menthone-based chiral nitrone and alkenes or alkynes under microwave activation afforded a series of enantiopure cycloadducts in good yields and with high stereoselectivity. Removal of the chiral auxiliary under acid-catalysis led to a new series of isoxazolidines and isoxazolines with the control of one, two or three stereogenic centers.