87505-04-2Relevant academic research and scientific papers
Regioselective and stereospecific halosilylating cleavage of the oxirane system of glycidol derivatives as an efficient strategy to C2-O-functionalized C3-vicinal halohydrins
Stamatov, Stephan D.,Stawinski, Jacek
, p. 2635 - 2643 (2008)
Glycidyl esters and ethers undergo a regioselective and stereospecific 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 (e.g. Bu4NX; X = Cl, Br, or I), followed by removal of the trifluoroacetyl transient protection, provides nearly quantitative access to the respective vicinal haloalkanols. Alternatively, C2-O-acylated vicinal halohydrins can be obtained in a highly chemo-/regiospecific manner by direct conversion of the trimethylsilyl protecting group into short- or long-chain ester functionalities by means of a three-component reagent: pyridine-carboxylic acid-TFAA. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
