Unexpected epimerization at C2 in the Horner-Wadsworth-Emmons reaction of chiral 2-substituted-4-oxopiperidines.
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.
Etayo
Pablo
P
Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragón, Instituto Universitario de Catálisis Homogénea, Universidad de Zaragoza-CSIC, E-50009 Zaragoza, Spain.
Badorrey
Ramón
R
Díaz-de-Villegas
María D
MD
Gálvez
José A
JA
D002244:Carbon / Q000737:chemistry*; D008968:Molecular Conformation; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D010880:Piperidines; D002244:Carbon