Diethyl α-(Methylthio)phosphonoacetic Acid: A New Bifunctional Reagent. Synthesis of Unsaturated Five- and Six-Membered Lactones

Marian Mikołajczyk; Wanda H. Midura

doi:10.1055/s-1991-20694

Synlett 1991; 1991(4): 245-247
DOI: 10.1055/s-1991-20694

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Diethyl α-(Methylthio)phosphonoacetic Acid: A New Bifunctional Reagent. Synthesis of Unsaturated Five- and Six-Membered Lactones

Marian Mikołajczyk^* , Wanda H. Midura

^*Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, PL-90-362 Łódź, Poland

Abstract

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The title compound 1 was prepared by addition of carbon dioxide to the α-carbanion derived from diethyl-phosphorylmethyl methyl sulfide. The Horner reaction of 1 gives α-methylthio-α,β-unsaturated carboxylic acids 5 in high yield. A new synthetic approach to unsaturated γ- and δ-lactones 6 is reported which involves esterification of 1 with α- and β-hydroxy aldehydes and ketones and subsequent intramolecular Horner reaction.

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