A chemoenzymatic approach to the synthesis of enantiomerically pure aza analogues of paraconic acid methyl ester and both enantiomers of methyl β-proline

F Felluga, G Pitacco, M Prodan, S Pricl, M Visintin…

Index: Felluga, Fulvia; Pitacco, Giuliana; Prodan, Massimo; Pricl, Sabrina; Visintin, Marco; Valentin, Ennio Tetrahedron Asymmetry, 2001 , vol. 12, # 23 p. 3241 - 3249

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Citation Number: 39

Abstract

Enantiopure methyl esters of 1-alkyl-5-oxo-3-pyrrolidinecarboxylic acids were obtained by enzymatic resolution of the corresponding chiral racemic mixtures. A particularly favourable interaction, also supported by molecular mechanics calculations, was observed between the 1-benzyl derivative and α-chymotrypsin, for which the enantiomeric ratio, E, exceeded 200. The absolute configurations of the lactams were determined by means of CD ...