Oxidation of alkyl trimethylsilyl ketene acetals with lead (IV) carboxylates

GM Rubottom, JM Gruber, R Marrero…

Index: Rubottom, George M.; Gruber, John M.; Marrero, Roberto; Juve, Henrik D.; Kim, Wan Chong Journal of Organic Chemistry, 1983 , vol. 48, # 25 p. 4940 - 4944

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Citation Number: 48

Abstract

A number of examples of the transformation of 1 into 3 are noted in Table I. With both a- acetoxy esters and a-benzoyloxy esters, the yields generated by the current method are uniformly high. NMR analysis of the crude reaction products obtained from the LTB reactions with la, b, d revealed only the corresponding a-benzoyloxy esters prior to fiial purification steps. Further, the use of methyl, ethyl, or tert-butyl in the alkoxy portion of 1 is compatible ...