An efficient synthesis of enantiomerically pure (R)-pipecolic acid, (S)-proline, and their N-alkylated derivatives.
Enantiomerically pure (R)-(+)-pipecolic acid was synthesized in four steps and 42% overall yield starting from dihydropyran and (R)-alpha-methylbenzylamine. A general short strategy is also described for preparing (S)-proline (47.5% overall yield) and derivatives.
Fadel
Antoine
A
Laboratoire de Synthèse Organique et Méthodologie, CNRS, UMR 8182, Institut de Chimie Moléculaire et des Matériaux d'Orsay, Bâtiment 420, Univ Paris-Sud, 91405 Orsay, France. antfadel@icmo.u-psud.fr
Lahrache
Nabil
N
D000478:Alkylation; D007202:Indicators and Reagents; D013058:Mass Spectrometry; D010627:Phenethylamines / Q000737:chemistry; D010875:Pipecolic Acids / Q000138:chemical synthesis* / Q000302:isolation & purification; D011392:Proline / Q000138:chemical synthesis* / Q000302:isolation & purification; D011714:Pyrans / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
D007202:Indicators and Reagents; D010627:Phenethylamines; D010875:Pipecolic Acids; D011714:Pyrans; D011392:Proline; C031345:pipecolic acid; C033198:1-phenethylamine