Abstract
A one-pot procedure for the conversion of carboxylic acids into homoallylic alcohols
under remarkably mild and selective conditions is described. The triethylammonium
salts of alkanoic acids are treated with Bu3 P/PhSeCl to afford the corresponding acyl selenides that are reduced to aldehydes
by tributyltin hydride under radical conditions. Direct in situ trapping of the aldehydes
by allylboronates affords the desired homoallylic alcohols. Preparation of optically
active alcohols by use of a tartrate-modified allylboronate is possible and the enantioselectivities
are similar to the ones obtained when isolated aldehydes are employed.
Key words
radicals - allylboronates - acyl selenides - allylation - carboxylic acid - reduction
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