On the Reaction of 1-Oxa-4-thiaspiro[4.5]decan-7-one with PhLi. A Reinvestigation

Abstract

Two diastereomeric alcohols are formed from the reaction of 1-oxa-4-thiaspiro[4.5]decan-7-one with PhLi as against the single diastereomer reported earlier. The diastereoselectivity achieved from PhMgBr is significantly higher than with PhLi. The use of Et(2)O/hexane = 2:1 as the solvent for the reaction with PhMgBr offered the highest (14:1) diastereocontrol.