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Synthesis 1994; 1994(10): 1072-1078
DOI: 10.1055/s-1994-25640
DOI: 10.1055/s-1994-25640
paper
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Efficient Synthesis of Substituted 2-Diethylphosphonylbuta-1,3-dienes
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Publication History
Publication Date:
27 September 2002 (online)
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.