A chemoenzymatic synthesis of optically active aza analogues of Quercus lactones

F Felluga, V Gombac, M Pavan, G Pitacco…

Index: Felluga, Fulvia; Gombac, Valentina; Pavan, Michela; Pitacco, Giuliana; Valentin, Ennio Tetrahedron Asymmetry, 2004 , vol. 15, # 1 p. 69 - 76

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Abstract

The synthesis of optically active 4-methyl-5-n-butyl-and 5-n-pentylpyrrolidin-2-ones, aza analogues of the corresponding Quercus lactones, has been achieved by a chemoenzymatic procedure, involving in the enantiodifferentiating step the enzymatic kinetic resolution of the corresponding γ-ketoester precursors, followed by reductive amination and subsequent cyclization of the enantiomerically pure hydrolysis products. The effect of the ...