Efficient Synthesis of Substituted 2-Diethylphosphonylbuta-1,3-dienes

Hashim Al-Badri; Elie About-Jaudet; Noël Collignon

doi:10.1055/s-1994-25640

Synthesis 1994; 1994(10): 1072-1078
DOI: 10.1055/s-1994-25640

paper

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Efficient Synthesis of Substituted 2-Diethylphosphonylbuta-1,3-dienes

Hashim Al-Badri^* , Elie About-Jaudet, Noël Collignon

^*Laboratoire des Composés Organophosphorés, INSA-IRCOF, BP 08, F-76131 Mont-Saint-Aignan Cedex, France

Abstract

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Numerous new substituted 2-diethylphosphonylbuta-1,3-dienes 5 bearing various aryl or alkyl substituents at the 1- and 4-positions were conveniently prepared from 2-diethylphosphonyl homoallylic alcohols 3, by stereospecific dehydration with dicyclohexylcarbodiimide in the presence of a catalytic amount of copper(II) chloride. In some cases, alcohols 3, resulting from the nucleophilic addition of lithiated allylic phosphonates 2 to various aromatic or aliphatic aldehydes, were isolated in a pure diastereomeric form, leading to diastereomerically pure dienes 5 upon dehydration.

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