A rearrangement of O,O-silylketene acetals leading to gamma-thiomethylation of butenoic acid derivatives

Jaroskova, Libuse;Bourgaux, Manuel;Wenkin, Isabelle;Ghosez, Léon
(1998) Tetrahedron Letters — Vol. 39, n° 20, p. 3157-3160 (1998)

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Authors
  • Jaroskova, LibuseUCLouvain
    Author
  • Bourgaux, ManuelUCLouvain
    Author
  • Wenkin, IsabelleUCLouvain
    Author
  • Ghosez, LéonUCLouvain
    Author
Abstract
Methylthiomethyl esters of alpha,beta-unsaturated acids 2 were converted into the corresponding ketene acetals 3 by O-silylation. Ketene acetals rearranged in refluxing toluene to give, after methanolysis, the corresponding gamma-methylthiomethyl substituted methyl esters 4. In the case of phenylthiomethylesters the products of alpha-substitution were observed. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
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Jaroskova, L., Bourgaux, M., Wenkin, I., & Ghosez, L. (1998). A rearrangement of O,O-silylketene acetals leading to gamma-thiomethylation of butenoic acid derivatives. Tetrahedron Letters, 39(20), 3157-3160. https://doi.org/10.1016/S0040-4039(98)00508-5 (Original work published 1998)