Arenesulfonate Derivatives of Homochiral Glycidol: Versatile Chiral Building Blocks for Organic Synthesis

Article abstract of DOI:10.1021/jo00267a014

The preparation of a series of crystalline arenesulfonate derivatives of enantiomerically enriched glycidol is described.The enhancement of optical purity by recrystallization was particularly successful for two of these derivatives, glycidyl tosylate and glycidyl 3-nitrobenzenesulfonate, which were obtained in 97 percent ee and 99 percent ee, respectively.Very high regioselectivity was observed in the reactions of these compounds with a variety of nucleophiles, including aryl oxides, Et2AlCN, organometallic reagents, and BH3-NaBH4.The application of this methodology to the synthesis of homochiral β-adrenergic blocking agents and homochiral terminal epoxides is discussed.