Chemoenzymatic preparation of non-racemic N-Boc-pyrrolidine-3,4-dicarboxylic acid 3-ethyl esters and their 4-hydroxymethyl derivatives

For the synthesis of metalloproteinase inhibitors the (R,R)- and (S,S)-monoethyl esters of N-Boe-pyrrolidine-3,4-dicarboxylic acid were prepared as key intermediates from the trans-diester racemate by two consecutive, highly selective enzymatic reactions. Reduction of the formed acids to the corresponding enantiopure hydroxymethyl derivatives ((R,R)- and (S,S)-ethyl N-Boc-4-hydroxymethyl-3-carboxylate) gives access to a new series of chiral building blocks. (C) 2003 Elsevier Science Ltd. All rights reserved.