Cinchona Alkaloid/Sulfinyl Chloride Combinations: Enantioselective Sulfinylating Agents of Alcohols

摘要

Chiral sulfinates play an important role in organic chemistry as key precursors in many chiral sulfoxides that are useful building blocks for biologically active molecules and natural products.Despite the development of many synthetic strategies to access chiral sulfinates in the last two decades,the most industrially viable procedure is still the one based on the resolution of diastereomeric sulfinates prepared from sulfinyl halides and chiral alcohols such as menthol and diacetone-D-glucose.On the other hand,the enantioselective sulfinylation reaction of achiral alcohols with racemic sulfinyl chlorides is particularly attractive.The initial report by Mikolajczyk and Drabowicz for the enantioselective sulfinylation reaction of alcohols with p-toluenesulfinyl chloride using chiral amines revealed limitations in enantioselectivities of the sulfinates.