Regioselective and Stereospecific Halosilylating Cleavage of the Oxirane System of Glycidol Derivatives as an Efficient Strategy to C2??O??Functionalized C3??Vicinal …

SD Stamatov, J Stawinski

Index: Stamatov, Stephan D.; Stawinski, Jacek European Journal of Organic Chemistry, 2008 , # 15 p. 2635 - 2643

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Citation Number: 8

Abstract

Abstract Glycidyl esters and ethers undergo a regioselective andstereospecific opening of the oxirane ring upon treatment with trimethylsilyl halides (TMSX, X= Cl, Br, or I) in the presence of pyridine to produce the corresponding C2-O-trimethylsilyl-3 (1)-halo-sn- glycerols in high yields. Trifluoroacetylation across the trimethylsilyloxy system of such C3- synthons with trifluoroacetic anhydride (TFAA) in the presence of a halide anion (eg Bu 4 ...