Asymmetric Synthesis of Homochiral 1,2-Diols via N-Boc Oxazolidines

Article abstract of DOI:10.1016/S0040-4039(00)76893-6

Diastereoisomerically pure N-Boc 2-acyloxazolidines were synthesized from phenylglyoxal and ethyl glyoxylate.Reaction of these heterocycles with Grignard reagents is highly stereoselective.Homochiral 1,2-diols were ultimately obtained after N-deprotection, hydrolysis and reduction of the intermediate α-hydroxy aldehyde.The asymmetric induction can be explained by a chelated model.