The Journal of Organic Chemistry

Catalytic asymmetric preparation of polyfunctional protected 1, 2-diols and epoxides

C Eisenberg, P Knochel

Index: Eisenberg, Christina; Knochel, Paul Journal of Organic Chemistry, 1994 , vol. 59, # 14 p. 3760 - 3761

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Citation Number: 41

Abstract

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