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Jung, M.E. et al.

Jung, Pontillo,

Facile preparation of allenic hydroxyketones via rearrangement of propargylic alcohols.

[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.[1]

References

Facile preparation of allenic hydroxyketones via rearrangement of propargylic alcohols. Jung, M.E., Pontillo, J. Org. Lett. (1999) [Pubmed]

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