Unexpected epimerization at C2 in the Horner–Wadsworth–Emmons reaction of chiral 2-substituted-4-oxopiperidines

Pablo Etayo; Ramón Badorrey; María D. Díaz-de-Villegas; José A. Gálvez

doi:10.1039/B608067G

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Unexpected epimerization at C₂ in the Horner–Wadsworth–Emmons reaction of chiral 2-substituted-4-oxopiperidines†

Pablo Etayo,^a Ramón Badorrey,^a María D. Díaz-de-Villegas*^a and José A. Gálvez*^a

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* Corresponding authors

^a Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragón, Instituto Universitario de Catálisis Homogénea, Universidad de Zaragoza-CSIC, E-50009 Zaragoza, Spain
E-mail: loladiaz@unizar.es; jagl@unizar.es
Fax: + 34 976761202
Tel: + 34 976762274

Abstract

The observed epimerization at C₂ in the Horner–Wadsworth–Emmons (HWE) reaction of chiral 2-substituted-4-oxopiperidines has been investigated and, on the basis of the experimental results, a mechanism for this unexpected process has been proposed.

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Supplementary files

Experimental details and full characterization data for all compounds PDF (53K)

Article information

DOI: https://doi.org/10.1039/B608067G
Article type: Communication
Submitted: 07 Jun 2006
Accepted: 27 Jun 2006
First published: 19 Jul 2006

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Chem. Commun., 2006, 3420-3422

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Unexpected epimerization at C₂ in the Horner–Wadsworth–Emmons reaction of chiral 2-substituted-4-oxopiperidines

P. Etayo, R. Badorrey, M. D. Díaz-de-Villegas and J. A. Gálvez, Chem. Commun., 2006, 3420 DOI: 10.1039/B608067G

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