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Detalle JF, Riahi A, Steinmetz V, et al. Mechanistic insights into the palladium-induced domino reaction leading to ketones from benzyl beta-ketoesters: first characterization of the enol as an intermediate. J Org Chem. 2004;69(20):6528-32doi: 10.1021/jo049464w.
Detalle, J. F., Riahi, A., Steinmetz, V., Hénin, F., & Muzart, J. (2004). Mechanistic insights into the palladium-induced domino reaction leading to ketones from benzyl beta-ketoesters: first characterization of the enol as an intermediate. The Journal of organic chemistry, 69(20), 6528-32. https://doi.org/10.1021/jo049464w
Detalle, Jean-François, et al. "Mechanistic insights into the palladium-induced domino reaction leading to ketones from benzyl beta-ketoesters: first characterization of the enol as an intermediate." The Journal of organic chemistry vol. 69,20 (2004): 6528-32. doi: https://doi.org/10.1021/jo049464w
Detalle JF, Riahi A, Steinmetz V, Hénin F, Muzart J. Mechanistic insights into the palladium-induced domino reaction leading to ketones from benzyl beta-ketoesters: first characterization of the enol as an intermediate. J Org Chem. 2004 Oct 01;69(20):6528-32. doi: 10.1021/jo049464w. PMID: 15387574.
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J Org Chem. 2004 Oct 01;69(20):6528-32. doi: 10.1021/jo049464w.

Mechanistic insights into the palladium-induced domino reaction leading to ketones from benzyl beta-ketoesters: first characterization of the enol as an intermediate.

The Journal of organic chemistry

Jean-François Detalle, Abdelkhalek Riahi, Vincent Steinmetz, Françoise Hénin, Jacques Muzart

Affiliations

  1. Unité Mixte de Recherche "Réactions Sélectives et Applications", CNRS-Université de Reims Champagne-Ardenne, B.P. 1039, 51687 Reims Cedex 2, France.

PMID: 15387574 DOI: 10.1021/jo049464w

Abstract

The monitoring by UV spectroscopy of the Pd-catalyzed hydrogenolysis in acetonitrile of 2-methyl-2-benzyloxycarbonyl-1-indanone and 2-methyl-2-benzyloxycarbonyl-1-tetralone showed the successive formation of corresponding beta-ketoacids and enols to deliver finally the ketones. Some factors which influence the stability of the intermediates are determined. In contrast to the above benzyl beta-ketoesters, the enol was not detected from benzyl (2-methylinden-3-yl) carbonate.

Copyright 2004 American Chemical Society

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