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

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

Chem Commun (Camb). 2006 Aug 28:(32):3420-2. doi: 10.1039/b608067g. Epub 2006 Jul 19.

Authors

Pablo Etayo¹, Ramón Badorrey, María D Díaz-de-Villegas, José A Gálvez

Affiliation

¹ Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragón, Instituto Universitario de Catálisis Homogénea, Universidad de Zaragoza-CSIC, E-50009 Zaragoza, Spain.

PMID: 16896481
DOI: 10.1039/b608067g

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbon / chemistry*
Molecular Conformation
Piperidines / chemical synthesis
Piperidines / chemistry*
Stereoisomerism

Substances

Piperidines
Carbon