Synthesis of enantiomerically pure (2R,5S)- and (2R,5R)-5-hydroxypipecolic acid from glycinate Schiff bases

Article abstract of DOI:10.1016/0957-4166(96)00332-1

An asymmetric synthesis of cis- and trans-5-hydroxy-(D)-pipecolic acid, starting from glycinate Schiff bases is described. The approach involves the stereoselective alkylation to generate an unsaturated side chain which on cyclisation leads to the desired trans- or cis-5-hydroxy-(D)-pipecolic acid.