The intramolecular Wadsworth-Emmons condensation of .gamma.-(acyloxy)-.beta.-ketophosphonates. A new route to 3(2H)-furanones

Paul Sampson; Vassilios Roussis; Gary J Drtina; Frederick L Koerwitz; David F Wiemer

doi:10.1021/jo00363a023

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The intramolecular Wadsworth-Emmons condensation of .gamma.-(acyloxy)-.beta.-ketophosphonates. A new route to 3(2H)-furanones

Journal article

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The intramolecular Wadsworth-Emmons condensation of .gamma.-(acyloxy)-.beta.-ketophosphonates. A new route to 3(2H)-furanones

Paul Sampson, Vassilios Roussis, Gary J Drtina, Frederick L Koerwitz and David F Wiemer

Journal of organic chemistry, Vol.51(13), pp.2525-2529

06/01/1986

DOI: 10.1021/jo00363a023

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Abstract

A series of γ-(acyloxy)-β-ketophosphonates has been synthesized, either from the corresponding a-iodo keto ester by an Arbuzov reaction or by acylation of an alkylphosphonate anion. When treated with potassium carbonate in DMF, these γ-(acyloxy)-β-ketophosphonates undergo an intramolecular Wadsworth-Emmons-type condensation to afford 3(2H)-furanones, providing a new route to this heterocyclic system. © 1986, American Chemical Society. All rights reserved.

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Title: Subtitle: The intramolecular Wadsworth-Emmons condensation of .gamma.-(acyloxy)-.beta.-ketophosphonates. A new route to 3(2H)-furanones
Creators: Paul Sampson
Vassilios Roussis
Gary J Drtina
Frederick L Koerwitz
David F Wiemer
Resource Type: Journal article
Publication Details: Journal of organic chemistry, Vol.51(13), pp.2525-2529
Publisher: American Chemical Society
DOI: 10.1021/jo00363a023
ISSN: 0022-3263
eISSN: 1520-6904
Language: English
Date published: 06/01/1986
Academic Unit: Neuroscience and Pharmacology; Chemistry
Record Identifier: 9984216716902771

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