1,3-Dipolar cycloaddition of enantiopure γ-oxygenated-α,β-unsaturated phenyl sulfones with nitrile oxides

The 1,3-dipolar cycloadditions of several enantiopure γ-oxygenated-α,β-unsaturated sulfones with acetonitrile and benzonitrile oxides have been studied. The reactions occurred at room temperature with moderate yields (31–65%), complete regioselectivity in favour of the isoxazolines with the phenylsu...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 1995-05, Vol.6 (5), p.1035-1038
Main Authors: de Blas, Jesús, Carretero, Juan C., Domínguez, Esteban
Format: Article
Language:English
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Summary:The 1,3-dipolar cycloadditions of several enantiopure γ-oxygenated-α,β-unsaturated sulfones with acetonitrile and benzonitrile oxides have been studied. The reactions occurred at room temperature with moderate yields (31–65%), complete regioselectivity in favour of the isoxazolines with the phenylsulfonyl group at C-4, and moderate or high anti-stereoselectivity. After reductive elimination of the sulfonyl group and further reduction of NO bond, enantiomerically pure β-hydroxyketones or 1,3-aminoalcohols were obtained. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/0957-4166(95)00118-9