Ring-opening of lactones with enolate nucleophiles: A simple access to functionalised β-ketoesters, β,δ-diketoesters and β-ketosulfoxides

S. Lanners; N. Khiri; G. Solladié; G. Hanquet

doi:10.1016/j.tetlet.2004.11.135

Ring-opening of lactones with enolate nucleophiles: A simple access to functionalised β-ketoesters, β,δ-diketoesters and β-ketosulfoxides

S. Lanners, N. Khiri, G. Solladié, G. Hanquet

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Abstract

γ-, δ- and ε-Lactones are readily opened by stabilised carbanions to the corresponding bis- or tris-silyl ethers, which can be selectively cleaved to 5- 6- or 7- silyloxy-3-ketoesters, 3,5-diketoesters, or 2-ketosulfoxides. © 2004 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	619-622
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	4
DOIs	https://doi.org/10.1016/j.tetlet.2004.11.135
Publication status	Published - 24 Jan 2005

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AB - γ-, δ- and ε-Lactones are readily opened by stabilised carbanions to the corresponding bis- or tris-silyl ethers, which can be selectively cleaved to 5- 6- or 7- silyloxy-3-ketoesters, 3,5-diketoesters, or 2-ketosulfoxides. © 2004 Elsevier Ltd. All rights reserved.

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Ring-opening of lactones with enolate nucleophiles: A simple access to functionalised β-ketoesters, β,δ-diketoesters and β-ketosulfoxides

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