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.