A stereoselective synthesis of tetrasubstituted β-tosyloxyacrylonitriles and β-siloxyacrylonitriles

Abstract

A method to stereoselectively access tetrasubstituted (E)- and (Z)-β-oxyacrylonitriles has been developed. The β-keto nitrile and β-keto amide starting materials are conveniently accessed from esters and nitriles, making this approach both convenient and straightforward. This methodology features moderate to excellent yield of products, excellent control of alkene geometry, and complete control of regiochemistry. Cross-coupling of β-tosyloxyacrylonitriles demonstrates the ability to access valuable stereodefined all-carbon tetrasubstituted acrylonitriles in excellent yield and stereocontrol.