Tetrahedron

Palladium (II)-catalyzed formation of γ-butyrolactones from 4-trimethylsilyl-3-alkyn-1-ols: Synthetic and mechanistic aspects

P Compain, J Goré, JM Vatèle

Index: Compain, Philippe; Gore, Jacques; Vatele, Jean-Michel Tetrahedron, 1996 , vol. 52, # 31 p. 10405 - 10416

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Citation Number: 34

Abstract

γ-butyrolactones are obtained in good yields from 4-trimethylsilyl-3-alkyn-1-ols via Wacker- type oxidation reaction. A mechanism is proposed for this transformation: it involves two successive trans-hydroxypalladations followed by a [PdXSiMe3] syn-elimination and explains why the presence of the silyl group is essential in such a process.