Efficient synthesis of β-hydroxy-sulfones via opening of epoxides with sodium sulfinates in ionic liquid [TPA][Pro]

Abstract

An efficient synthesis of β-hydroxy-sulfones is described by the reaction of sodium sulfinates with epoxides in ionic liquid [TPA][Pro] as an efficient reaction medium to afford the corresponding β-hydroxy-sulfones in excellent yields.

Copper(i)-mediated synthesis of β-hydroxysulfones from styrenes and sulfonylhydrazides: an electrochemical mechanistic study

“…b-Hydroxysulfones are of great interest as structural units of antifungal 1 and antitumor 2 compounds, they are known as intermediates in the synthesis of lactones 3 and unsymmetrical alkenes. 4 Traditionally b-hydroxysulfones are obtained through the nucleophilic addition of sulnates to epoxides, [5][6][7][8] reduction of b-ketosulfones 9,10 and hydroxylation of a,b-unsaturated sulfones. 11 Over the last few years, several oxidative strategies to prepare b-hydroxysulfones from olens have been established.…”

Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds

“…A convenient ring-opening of epoxides occurred with sodium sulfinates using ionic liquid, tetrapropyl ammonium hydroxide and l -proline [TPA][Pro] in aqueous medium at 80 °C for the synthesis of β-hydroxy sulfones ( Scheme 157 ). 222 Venkateswarlu and co-workers showed the reasonable generality for the regioselective sulfonylation of various mono- and di-substituted epoxides with different sodium aryl and alkyl sulfinates to give the corresponding β-hydroxy sulfones in good to high yields.…”