Stereoselective cycloaddition of nitrile oxides to a dispiroketal-protected but-3-ene-1,2-diol

The influence of a dispiroketal protecting group on the π-facial selectivity of nitrile oxide cycloaddition to S-but-3-ene-1,2-diol has been investigated. Ethoxycarbonylformonitrile oxide and benzonitrile oxide undergo regiospecific and diasteroeselective addition to alkene 7 to afford isoxazolines...

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Published in:Tetrahedron: asymmetry 1995-11, Vol.6 (11), p.2723-2730
Main Authors: Gravestock, Michael B., Paton, R.Michael, Todd, Christine J.
Format: Article
Language:English
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Summary:The influence of a dispiroketal protecting group on the π-facial selectivity of nitrile oxide cycloaddition to S-but-3-ene-1,2-diol has been investigated. Ethoxycarbonylformonitrile oxide and benzonitrile oxide undergo regiospecific and diasteroeselective addition to alkene 7 to afford isoxazolines 11 and 12. The major adducts ( 11a and 11b) are formed with 44% and 50% d.e. respectively, and in each case have S-configuration at C-5, the new stereogenic centre. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/0957-4166(95)00362-S