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

摘要

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