Chemoenzymatic synthesis of orthogonally protected (3R,4R)- and (3S,4S)-trans-3-amino-4-hydroxypyrrolidines

Several orthogonally protected racemic trans-3-amino-4-hydroxypyrrolidines have been easily prepared from N-Cbz-3,4-epoxypyrrolidine. Resolution of each racemic compound was accomplished by means of lipase-catalyzed aminolysis, transesterification or hydrolysis reactions. In most cases, the corresponding remaining substrates and the products were obtained with very high enantiomeric excesses. (C) 2013 Elsevier Ltd. All rights reserved.