Sign in
Back
Synthesis and reactivity of N-sugar-maleimides: an access to novel highly substituted enantiopure pyrazolines
Journal article   Peer reviewed

Synthesis and reactivity of N-sugar-maleimides: an access to novel highly substituted enantiopure pyrazolines

Naoufel Ben Hamadi and Moncef Msaddek
Tetrahedron: asymmetry, Vol.23(24), pp.1689-1693
31/12/2012
DOI: https://doi.org/10.1016/j.tetasy.2012.11.005

Abstract

Chemistry Chemistry, Inorganic & Nuclear Chemistry, Organic Chemistry, Physical Physical Sciences Science & Technology
Two diastereomeric isoxazolines were synthesized in a stereoselective manner with 6.64-20.36% diastereoisomeric excess. The cycloaddition of N-sugar-maleimide in the presence of MgBr2 afforded isoxazolines with high diasterioselectivities (76-84% de). The 1,3-dipolar cycloaddition reaction was diastereospecific and enantiomerically pure (3R,45,5S,6S,3aR,6a5)-pyrazolines were obtained from N-sugar-maleimides via 1,3-proton migration. (C) 2012 Elsevier Ltd. All rights reserved.

Metrics

1 Record Views

Details