Regio- and diastereoselective synthesis of unsymmetrical 1,4-diketone-derived (Z)-monosilyl enol ethers via siloxyallylpotassium intermediates

Abstract

This paper describes the regio- and diastereoselective synthesis of unsymmetrical 1,4-diketone-derived (Z)-monosilyl enol ethers from 1-arylallyloxysilanes and Weinreb amides using (trimethylsilyl)methylpotassium as a base. The metalation of 1-arylallyloxysilanes to generate siloxyallylpotassiums is the key step in this transformation. The products can be transformed into diverse α-monofunctionalized unsymmetrical 1,4-diketones.