Abstract
Abstract Recent interest in developing methods for the synthesis of α-hydroxy esters has focused on both the direct oxygenation of ester enolates1 and the treatment of ester enolates with MoOPh (MoO5·Py·HMPA).2 Based upon our previous observations that enol silyl ethers3 and ketene bis(trimethylsilyl) acetals4 react with m-chloroperbenzoic acid (MCPBA) to afford high yields of the corresponding α-hydroxy carbonyl compounds we have attempted to extend the scope of this type of oxidation to include alkyl trimethylsilyl ketene acetals 1. We would like to report here that the treatment of 1 with MCPBA followed by treatment of the crude reaction mixture with triethylammonium fluoride leads to the high yield production of α-hydroxy esters 2. Since 1 are easily obtained from a variety of esters by using the method reported by Ainsworth5 the current procedure would appear to be quite general for the production of 2. Some representative examples are given in the Table. In the cases cited yields are uniformly high ...
Published Version
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