Selective deprotection of alkyl esters using magnesium methoxide

The use of magnesium methoxide for the deprotection of alkyl esters is described. This mild reagent provides a good method to cleave esters efficiently and more importantly, allows for effective differentiation between two different esters. The order of the reactivity of this reagent towards acyl cl...

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Bibliographic Details
Published inTetrahedron letters Vol. 37; no. 4; pp. 455 - 458
Main Authors Yao-Chang, Xu, Bizuneh, Amsalu, Walker, Clint
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.01.1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MILD
METHANOL
SUGAR CHEMISTRY
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Summary:The use of magnesium methoxide for the deprotection of alkyl esters is described. This mild reagent provides a good method to cleave esters efficiently and more importantly, allows for effective differentiation between two different esters. The order of the reactivity of this reagent towards acyl cleavages was found to be: p-nitrobenzoate>acetate>benzoate>pivaloate>>acetamide. The use of magnesium methoxide for the deprotection of alkyl esters is described. This mild reagent provides a good method to cleave esters efficiently and more importantly, allows for effective differentiation between two different esters. The order of the reactivity of this reagent towards ester cleavages was found to be: p-nitrobenzoate > acetate > benzoate > pivaloate >> acetamide.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(95)02197-3