Catalytic Asymmetric Preparation of Polyfunctional Protected 1,2-Diols and Epoxides

Article abstract of DOI:10.1021/jo00093a005

α-Trialkylsiloxy aldehydes 4a,b add functionalized diorganozincs in the presence of catalytic amounts of (1R,2R)-bis(trifluoromethanesulfonamido)cyclohexane (8 mol percent), affording protected 1,2-diols in 39-89percent yield and 70-94percent ee.The conversion of the monosilylated 1,2-diols to functionalized chiral epoxides has been demonstrated.