Tetrahedron Letters

Studies on DMDO-mediated benzylidene acetal oxidation

DK Mycock, AE Sherlock, PA Glossop, CJ Hayes

Index: Mycock, David K.; Sherlock, Alexandra E.; Glossop, Paul A.; Hayes, Christopher J. Tetrahedron Letters, 2008 , vol. 49, # 45 p. 6390 - 6392

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Citation Number: 11

Abstract

We have shown that dimethyldioxirane (DMDO) can be used to effect an oxidative partial deprotection of benzylidene acetals derived from both 1, 2-and 1, 3-diols to afford hydroxy benzoate products. A wide range of functional groups are tolerated, and good to excellent yields are usually observed. The reactions are easy to perform and produce little waste other than acetone.