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

DOI: 10.1016/0040-4020(96)00567-4

Source and publish data:

Tetrahedron p. 10405 - 10416 (1996)

Update date:2022-08-03

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Authors:

Compain, Philippe

Gore, Jacques

Vatele, Jean-Michel

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Article abstract of DOI:10.1016/0040-4020(96)00567-4

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.

Full text of DOI:10.1016/0040-4020(96)00567-4

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