A facile synthesis of 3,4-dimercaptofurans via sulfenylation of (E)-β-chlorovinyl ketones and 1,2-sulfur migration

Abstract

The one-pot sulfenylation of (E)-β-chlorovinyl ketones was investigated under soft α-vinyl enolization conditions. Modulating the nature of nucleophilic species using a “hard” base the regioselective formation of α,γ-dithio-allenyl ketones has been achieved, where the thermodynamic control was mimicked by the presence of Et₃N·HCl. The sulfenylated products, α,γ-dithio-allenyl and α,α-dithio-propargyl ketones, smoothly underwent cycloisomerization to 3,4-dimercaptofurans via a novel 1,2-sulfur migration in excellent yields.