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Synthesis of δ-lactones from 2-alkynyl epoxides and 4-alkynyl-1,3-dioxolan-2-ones by palladium catalysed carbonylation and conjugate nucleophilic addition

Lookup NU author(s): Dr Julian Knight, Dr Simon Harwood

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Abstract

Synthesis of δ-lactones from 2-alkynyl epoxides and 4-alkynyl-1,3-dioxolan-2-ones by palladium catalysed carbonylation and conjugate nucleophilic addition was investigated. The stereocontrolled conjugate addition of nucleophiles to the electron deficient 2,3-double bond of allenes gave γ,δ-unsaturated δ-lactones in the case of lithium dimethylcuprate. It was found that the palladium catalysed carbonylation of alkynyldioxolanones and alkynyl epoxides proceeded in good yields under very mild conditions.

Publication metadata

Author(s): Knight JG, Ainge SW, Baxter CA, Eastman TP, Harwood SJ

Publication type: Article

Publication status: Published

Journal: Journal of the Chemical Society, Perkin Transactions 1

Year: 2000

Issue: 19

Pages: 3188-3190

ISSN (print): 1470-4358

ISSN (electronic): 1364-5463

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/b006927m

DOI: 10.1039/b006927m

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