Stereoselective Synthesis of β-Alkoxy- and β-Alkylthio-Acrylic Esters and Amides from β-Tosylacrylic Derivatives

Article abstract of DOI:10.1016/0040-4020(95)00077-L

A simple and stereoselective synthesis of β-alkoxy- and β-alkylthio-acrylic esters and amides (8) by nucleophilic vinylic substitution of the tosyl group by sodium alcoholates and thiolates of (E)-β-tosylacrylic derivatives (7), prepared by iodosulfonylation-dehydroiodination of acrylic compounds, is described.This methodology is applied to the synthesis of sinharine (8eh) a natural antifungal isolated from glycosmis cyanocarpa.