Asymmetric sulfenylation of 3-CF3-Oxindoles through organocatalysis with a quinidine derivative. Issue 26 (28th June 2017)

• Record Type: Journal Article
• Authors: E, Yidan; Yuan, Teng; Yin, Liang; Xu, Youjun
• Is Part Of: Tetrahedron letters. Volume 58:Issue 26(2017)
• Page Start: 2521
• Page End: 2524
• Publication Date: 2017-06-28
• Subjects: 3-CF3-oxindole -- Asymmetric sulfenylation -- Quinidine derivative; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.05.015
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: 3-CF3 -oxindoles were obtained in good yield. Asymmetric sulfenylation of 3-CF3 -oxindole was obtained in 84% yield and with 94% ee. The electro-donating groups of 3-CF3 -oxindoles were well tolerated. The electro-donating groups of sulfenylation reagents were well tolerated. The electro-withdrawing groups of sulfenylation reagents were also well tolerated. Abstract: An asymmetric sulfenylation of 3-CF3 -oxindoles catalyzed by a quinidine derivative was described. 3-CF3 -oxindoles with electro-donating groups led to corresponding products in good yield and with good enantioselectivity while 3-CF3 -oxindoles bearing electro-withdrawing groups were not competent substrates due to its significant decomposition at the optimal reaction conditions. As for the sulfenylation reagents based on thiophenol, both electro-donating groups and electro-withdrawing groups were well tolerated.