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Synthesis 1995; 1995(11): 1401-1404
DOI: 10.1055/s-1995-4122
DOI: 10.1055/s-1995-4122
paper
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Synthesis, Acetylation and Silylation of (1E)-2-Diethoxyphosphonylbuta-1,3-dien-1-ols: A Convenient Route to New, Activated Dienylphosphonates
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Publication History
Publication Date:
31 December 2000 (online)
Lithiated carbanions of allylic phosphonates 1 showed strict α-regioselectivity in their reaction with ethyl formate, giving stereoselectively (1E)-2-phosphonodienols 3b and 3d, or a mixture of 3c with its tautomeric aldehyde 4c, or the conjugated aldehyde 5 resulting from the prototropy of the enol 3a. All these compounds, obtained in high yields, were readily transformed into the corresponding stable O-acetylated derivatives 6 or into the O-silylated derivatives 7, whose stability depends on the silicon substituents.
O-Substituted 2-phosphonodienols 6 and 7 are conveniently synthesized in two steps from allylphosphonates 1