Abstract
A convenient reaction condition for the regioselective thiolysis of epoxides using a series of thiols in water without applying any catalyst has been demonstrated with excellent yields.
Highlights
Ring opening of epoxides with thiols is one of the most practically used protocols for the synthesis of β-hydroxy sulfides for use in organic synthesis.[1] β-Hydroxy sulfides serve as important intermediates for the synthesis of several molecules of biological interest and natural products.[2]
We report a practical methodology for the preparation of β-hydroxy sulfides by thiolysis of epoxides in water without using any catalyst or special technical requirement (Scheme 1)
In a set of initial experiments, a mixture of fructose derived terminal epoxide (Table 1, entry 2) and a varied quantity of thiophenol in water was allowed to stir at different temperatures ranging from room temperature to 80 °C
Summary
Ring opening of epoxides with thiols is one of the most practically used protocols for the synthesis of β-hydroxy sulfides for use in organic synthesis.[1] β-Hydroxy sulfides serve as important intermediates for the synthesis of several molecules of biological interest and natural products.[2]. A number of reports appeared for the thia-Michael[8] and aza-Michael[9] reaction and ring opening of epoxides with amines[10] in water without using any catalyst. Epoxides for the preparation of β-hydroxy sulfides in water without using any catalyst has not been attempted before.
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