A One-Pot Conversion of Carboxylic Acids into Homoallylic Alcohols

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 Bu₃P/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

References

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1

New address: Department für Chemie und Biochemie, Universität Bern, Freiestrasse 3, 3000 Bern 9, Switzerland. E-mail: [e-mail].

12

Roush (ref. [9f] ) has reported that allylation reactions are usually higher yielding in toluene than in THF.