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Synthesis 2008(24): 3951-3956  
DOI: 10.1055/s-0028-1083242
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Novel and Convenient Synthesis of Cyclopent-1-enecarboxylates by an ­Intramolecular Horner-Wadsworth-Emmons Reaction

Henryk Krawczyk*, Łukasz Albrecht
Institute of Organic Chemistry, Technical University (Politechnika), Żeromskiego 116, 90-924 Łódź, Poland
Fax: +48(42)6365530; e-Mail: henkrawc@p.lodz.pl;
Further Information

Publication History

Received 21 August 2008
Publication Date:
01 December 2008 (online)

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Abstract

A general and efficient method for the preparation of 2-diethoxyphosphoryl-6-oxohexanoates is presented. This approach is based on the Michael addition of [2-(1,3-dioxolan-2-yl)ethyl]magnesium bromide to various 3-substituted tert-butyl (E)-2-(diethoxyphosphoryl)alk-2-enoates as a key step. Application of the 2-diethoxyphosphoryl-6-oxohexanoates obtained in the intramolecular Horner-Wadsworth-Emmons reaction for the preparation of 5-substituted tert-butyl cyclopent-1-enecarboxylates is also reported.

Key words

Michael reaction - intramolecular Horner-Wadsworth-Emmons reaction - cyclopent-1-enecarboxylates - phosphonates - 6-oxoalkanoates

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