Nucleophilic acyl substitutions of esters with protic nucleophiles mediated by amphoteric, oxotitanium, and vanadyl species

CT Chen, JH Kuo, CH Ku, SS Weng…

Index: Chen, Chien-Tien; Kuo, Jen-Huang; Ku, Cheng-Hsiu; Weng, Shiue-Shien; Liu, Cheng-Yuan Journal of Organic Chemistry, 2005 , vol. 70, # 4 p. 1328 - 1339

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Citation Number: 37

Abstract

A diverse array of oxometallic species were examined as catalysts in nucleophilic acyl substitution (NAS) reactions of methyl (or ethyl) esters with protic nucleophiles. Among them, oxotitanium acetylacetonate (TiO (acac) 2) and vanadyl chloride (VOCl2-(THF) x) served as the most efficient and water-tolerant catalysts. Transesterifications of methyl and/or ethyl esters with functionalized (including acid-or base-sensitive) 1° and 2° alcohols can be ...