Facile preparation of allenic hydroxyketones via rearrangement of propargylic alcohols |
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Authors: | Jung M E Pontillo J |
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Institution: | Department of Chemistry and Biochemistry, University of California, Los Angeles 90095-1569, USA. jung@chem.ucla.edu |
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Abstract: | formula: see text] Treatment of tertiary propargylic alcohols 13 with 3-diazo-2-butanone 6 and catalytic dirhodium tetraacetate in benzene gave good yields of the diastereomeric allenic hydroxyketones 14, with, in some cases, good diastereocontrol. These products are presumably formed via the 2,3]-sigmatropic rearrangement of an alpha-propargyloxy enol derivative. This reaction has been extended to the preparation of homoallylic hydroxyketones from allylic alcohols by reaction with 6 and the rhodium catalyst. |
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