Stereoselective syntheses of L-pipecolic acid and (2S,3S)-3-hydroxypipecolic acid from a chiral N-imino-2-phenyl-1,2-dihydropyridine intermediate.
Stereoselective syntheses of L-pipecolic acid and (2S,3S)-3-hydroxypipecolic acid were achieved from a chiral N-imino-2-phenyl-1,2-dihydropyridine intermediate. The 3-hydroxy substituent of the latter amino acid was introduced by hetero-Diels-Alder reaction of singlet oxygen with the 1,2-dihydropyridine.
Lemire
Alexandre
A
Département de chimie, Universit de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada, H3C 3J7.
Charette
André B
AB
D004095:Dihydropyridines / Q000737:chemistry*; D015394:Molecular Structure; D010875:Pipecolic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
C529304:3-hydroxypipecolic acid; D004095:Dihydropyridines; D010875:Pipecolic Acids