N-Benzyl-3-(Tri-n-butylstannyl)Thiopropionamide as Thiohomoenolate Synthon. Application to a Synthesis of Some Heterocycles

Abstract

N-Benzyl-3-(tri-n-butylstannyl)thiopropionamide undergoes metal-exchange with n-butyllithium. The resulting thiohomoenolate dianion reacts with electrophiles (aldehydes and ketones) to give the γ-hydroxythioamides, which are transformed into lactones, iminothiolactones, and thiolactams with simple elaboration.