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Issue 19, 2000
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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

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Abstract

Palladium catalysed carbonylation of both 4-alkynyl-1,3-dioxolan-2-ones and alkynyl epoxides occurs under mild conditions to give methyl 5-hydroxy-2,3-dienoates which are converted to γ,δ-unsaturated δ-lactones by tandem conjugate addition–cyclisation with lithium dimethylcuprate or to methyl (E )-5-hydroxypent-3-enoates by stereoselective reduction with sodium borohydride.

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Article information


Submitted
21 Jul 2000
Accepted
24 Aug 2000
First published
11 Sep 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 3188-3190
Article type
Communication

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

J. G. Knight, S. W. Ainge, C. A. Baxter, T. P. Eastman and S. J. Harwood, J. Chem. Soc., Perkin Trans. 1, 2000, 3188
DOI: 10.1039/B006927M

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