Diastereoselective synthesis of (2S,5R)-5-hydroxypipecolic acid and 6-substituted derivatives.
[reaction: see text] Herein, we report a diastereoselective synthesis of the natural product (2S,5R)-5-hydroxypipecolic acid and 6-substituted derivatives thereof. The key step in the synthetic sequence is a novel highly diastereoselective epoxidation reaction of an enantiomerically pure cyclic enamide intermediate.
Botman
Peter N M
PN
Chiralix B.V., P.O. Box 31070, 6503 CB Nijmegen, The Netherlands.
Dommerholt
F Jan
FJ
de Gelder
René
R
Broxterman
Quirinus B
QB
Schoemaker
Hans E
HE
Rutjes
Floris P J T
FP
Blaauw
Richard H
RH
D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D010875:Pipecolic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D010875:Pipecolic Acids; C053574:5-hydroxypipecolic acid