Addition of Bis-sulfinyl Anions to Ketones: Stereoselective Synthesis of Allylic Alcohols through Evans-Mislow Rearrangement Based Domino Reactions

Abstract

Enantiopure cyclic allylic alcohols were obtained from cyclic ketones and bis-sulfoxides through a domino reaction mixing anionic and concerted elementary steps. Total transfer of chirality was achieved, presumably through cooperative effects of both sulfoxides units. Depending on the ring size, both sulfinyl groups could be converted, giving C ₂-symmetric bis-allylic alcohols.

alkenation - carbanion - pericyclic reaction - sulfoxide - sulfur

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