A new route to (2S,4R)- and (2R,4S)-4-hydroxypipecolic acid

Article abstract of DOI:10.1016/S0957-4166(99)00458-9

Both enantiomers of cis-4-hydroxypipecolic acid have been prepared by asymmetric synthesis using (S)- or (R)-glycidol as the chiral source, and involving a stereoselective hydrogenation of a six-membered cyclic imine. The latter is obtained by reduction and cyclization of a cyano β-hydroxy ketone.