Issue 19, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

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

Julian G. Knight,*a   Simon W. Ainge,a   Carl A. Baxter,a   Timothy P. Eastmana  and  Simon J. Harwooda  

* Corresponding authors

a Department of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, UK
E-mail: J.G.Knight@ncl.ac.uk

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

DOI
https://doi.org/10.1039/B006927M
Article type
Communication
Submitted
21 Jul 2000
Accepted
24 Aug 2000
First published
11 Sep 2000

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

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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

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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