Tetrahedron: Asymmetry

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

RMR Sarmiento, B Wirz, H Iding

Index: Rodriguez Sarmiento, Rosa Maria; Wirz, Beat; Iding, Hans Tetrahedron Asymmetry, 2003 , vol. 14, # 11 p. 1547 - 1551

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Citation Number: 9

Abstract

For the synthesis of metalloproteinase inhibitors the (R, R)-and (S, S)-monoethyl esters of N- Boc-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 ...