[3,3]-Sigmatropic rearrangement of allenic alcohols: stereoselective synthesis of 1,3-diene-2-ol sulfonates

Abstract

An efficient synthetic pathway to 1,3-diene-2-ol sulfonates involving the [3,3]-sigmatropic rearrangement of allenic alcohols with sulfonic acids under mild reaction conditions is described. These products can easily undergo reduction or transition-metal catalyzed cross-coupling reactions to yield a series of stereodefined multisubstituted 1,3-dienes.