An Efficient and Chemoselective Method for Synthesis of 1,3-Oxathiolanes from Aldehydes and their Deprotection Catalyzed by V(HSO4)3

摘要

The carbonyl group plays a predominant role in organic synthesis due to its electrophilic nature. One of the major common problems during many multi-step syntheses in organic, medicinal, carbohydrate and drug design chemistry is how to protect the carbonyl group from nucleophilic attack until its electrophilic properties could be utilized. Therefore, the protection and deprotcetion of carbonyl groups remain an area of interest in synthetic organic chemistry. Among the carbonyl protecting groups, 1,3-oxathiolanes are important class of compounds that are more stable than corresponding O,O-acetals under acidic conditions and compared with S,S-acetals are more easily deprotected. In addition, 1,3-oxathiolanes can be utilized as acylation equivalents in C-C bond formation. Moreover, the chiral 1,3-oxathiolanes are valuable synthons for enantioselective synthesis of α-hydroxyaldehydees.