One-pot synthesis of thia-Michael products from thio acids, epoxides, and electron-deficient alkenes promoted by a silica gel/Et₃N combined catalyst

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• 作者：Mohammad Abbasi ; ^{abbassi@pgu.ac.ir}
• 关键词：Michael addition ; Conjugate addition ; Thiol ; Silica gel ; Epoxide
• 刊名：Tetrahedron Letters
• 出版年：2012
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：11 July, 2012
• 卷：53
• 期：28
• 页码：3683-3685
• 文件大小：3346 K

摘要

An efficient method for the one-pot production of thia-Michael adducts using thio acids, epoxides, and electron-deficient alkenes is described. Epoxides quickly underwent nucleophilic ring-opening with thio acids on the silica gel surface at room temperature under solvent-free conditions to yield 尾-hydroxy thioester intermediates. After addition of an electron-deficient alkene and a catalytic amount of Et₃N to the reaction mixture, the 尾-acyloxy mercaptans were generated in situ and subsequently underwent thia-Michael addition reactions to produce the corresponding adducts in good to excellent yields.