Abstract
Opening of epoxides with various S-alkylisothiouronium salts as thiol equivalent in water has been carried out in excellent yield following an environmentally benign odorless reaction condition. Yields were excellent in every case.
Highlights
Introduction βHydroxy sulfides serve as important intermediates for the synthesis of several bioactive and medicinally important natural products.[1]
They can be synthesized by the ring opening of epoxides with thiols in the presence of a base[2] or a homogeneous and heterogeneous acidic catalysts 3 in organic solvents
Despite their synthetic utilities most of the reaction conditions suffer from a number of drawbacks, which include the use of obnoxious thiols, strong and non-selective acidic catalysts, expensive and toxic reagents, organic solvents, low yield and long reaction time
Summary
Introduction βHydroxy sulfides serve as important intermediates for the synthesis of several bioactive and medicinally important natural products.[1]. Reactions using water as reaction media.[9] We report a simple and practical method for the synthesis of β-hydroxy sulfides by opening of oxiranes with in situ generated thiolate ions using S-alkylisothiouronium salts[10] catalyzed by sodium hydroxide in water (Scheme 1).
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