Base-catalyzed bis-sulfenylation of γ-substituted butenolides for the synthesis of α, α-bisthiofunctionalized butenolide derivatives. Issue 36 (7th September 2017)

• Record Type: Journal Article
• Authors: Zhao, Jian-Qiang; Luo, Shu-Wen; Zhang, Xiao-Mei; Xu, Xiao-Ying; Zhou, Ming-Qiang; Yuan, Wei-Cheng
• Is Part Of: Tetrahedron. Volume 73:Issue 36(2017)
• Page Start: 5444
• Page End: 5450
• Publication Date: 2017-09-07
• Subjects: Bis-sulfenyaltion -- Butenolides -- N-(aryl(alky)sulfanyl)succinides -- N-(phenylsulfanyl)phthalimides -- α-sulfenylated butenolides; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.07.053
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A method for the synthesis of α, α -bisthiofunctionalized butenolide compounds has been successfully developed. The bis-sulfenylation of γ -substituted butenolides at α-position is promoted by using triethylamine as the catalyst and N -(aryl(alkyl)sulfanyl)succinimides or N -(phenylsulfanyl)phthalimides as sulfenylating reagents under mild reaction conditions. A range of α -sulfenylated butenolide derivatives could be smoothly obtained in moderate to excellent yields. A preliminary attempt at the catalytic asymmetric α -sulfenylation of α -methyl- γ -phenyl-substituted butenolide was also conducted and afforded promising enantioselectivity. Graphical abstract: