Selective carbophilic addition of organolithiums to thioamides. A novel synthesis of unsymmetrical ketones and α-alkylated amines

Abstract

Thioamides, readily available from aldehydes, sulfur and secondary amines, can be converted to unsymmetrical ketones by the carbophilic addition of organolithiums to the thiocarbonyl group. Reduction of the intermediates with lithium aluminum hydride gives α-alkylated or α-arylated amines.