Tetrahedron

Diastereoselective synthesis of γ-hydroxy α, β-epoxyesters and their conversion into β-hydroxy α-sulfenyl γ-butyrolactones

S Rodríguez, M Kneeteman, J Izquierdo, I López…

Index: Rodriguez, Santiago; Kneeteman, Maria; Izquierdo, Javier; Lopez, Irakusne; Gonzalez, Florenci V.; Peris, Gabriel Tetrahedron, 2006 , vol. 62, # 48 p. 11112 - 11123

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Citation Number: 16

Abstract

The diastereoselectivity of the nucleophilic epoxidation of γ-hydroxy-α, β-unsaturated esters has been studied. The γ-hydroxy-α, β-unsaturated esters were obtained through treatment of ethyl (E)-4-oxo-2-butenoate with the corresponding Grignard reagent and were used as a racemic mixture. The resulting γ-hydroxy α, β-epoxyesters were treated with thiophenol for transformation into α-phenylsulfanyl trisubstituted γ-butyrolactones. The syn, syn-lactones ...