Unusual and efficient ( Z)-stereoselective peterson synthesis of 2-diethoxyphosphonyl-1-alkoxy-3-methylpenta-1,3-dienes. Their use in the diels-alder reaction

The lithiated anion of diethyl α-trimethylsilyl-prenylphosphonate, readily in situ generated from diethyl prenylphosphonate, reacts smoothly with various alkyl formates to give the title compounds with exclusive 1-( Z)-geometry and in high isolated yield. The [4 + 2] cycloaddition reaction of dienes...

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Bibliographic Details
Published in:Tetrahedron letters 1996-04, Vol.37 (17), p.2951-2954
Main Authors: Al-Badri, Hashim, About-Jaudet, Elie, Collignon, Noël
Format: Article
Language:English
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Summary:The lithiated anion of diethyl α-trimethylsilyl-prenylphosphonate, readily in situ generated from diethyl prenylphosphonate, reacts smoothly with various alkyl formates to give the title compounds with exclusive 1-( Z)-geometry and in high isolated yield. The [4 + 2] cycloaddition reaction of dienes 3 with electron-deficient dienophiles is described. Title dienes 3 were efficiently prepared from phosphonate 1c, by a one pot synthesis and used to give new cycloadducts 4–6.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(96)00452-2