Chemoenzymatic synthesis of optically active α-methylene-γ-carboxy-γ-lactams and γ-lactones

…, L Fanfoni, F Felluga, G Pitacco, E Valentin

Index: Bertoli, Annalisa; Fanfoni, Lidia; Felluga, Fulvia; Pitacco, Giuliana; Valentin, Ennio Tetrahedron Asymmetry, 2009 , vol. 20, # 19 p. 2305 - 2310

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Citation Number: 13

Abstract

Three α-methylene-γ-carbomethoxy-γ-butyrolactams (methyl α-methylene-pyroglutamates) 11, 12 and 13, differing in the substitution at the heterocyclic nitrogen, as well as the structurally related γ-lactones 14 and 15 were synthesised and resolved enzymatically by hydrolysis of their ester function, mediated by commercially available hydrolytic enzymes. In particular, the α-chymotrypsin proved to be active to all the substrates examined, ...