A facile synthesis of 3,4-dimercaptofurans via sulfenylation of (E)-β-chlorovinyl ketones and 1,2-sulfur migration?
Organic & Biomolecular Chemistry Pub Date: 2017-01-31 DOI: 10.1039/C6OB02772E
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.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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