Organocatalytic asymmetric [3+2]-cycloaddition of 3-isothiocyanato oxindoles with 1, 3, 5-trisubstituted-hexahydro-1, 3, 5-triazines to access spiro-imidazolidinethione-oxindoles. Issue 40 (4th October 2019)

• Record Type: Journal Article
• Authors: Zhang, Chuan-Bao; Dou, Pei-Hao; You, Yong; Wang, Zhen-Hua; Zhou, Ming-Qiang; Xu, Xiao-Ying; Yuan, Wei-Cheng
• Is Part Of: Tetrahedron. Volume 75:Issue 40(2019)
• Publication Date: 2019-10-04
• Subjects: Asymmetric [3+2]-cycloaddition -- Organocatalysis -- 1, 3, 5-Trisubstituted-hexahydro-1, 3, 5-triazines -- Spirooxindoles; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.130571
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: An efficient asymmetric [3 + 2]-cycloaddition reaction of 3-isothiocyanato oxindoles and formaldimines in-situ generated from 1, 3, 5-trisubstituted-hexahydro-1, 3, 5-triazines with a cinchona alkaloid-derived thiourea as the catalyst has been developed. A range of biologically important spiro-imidazolidinethione-oxindoles were obtained in excellent yields with good enantioselectivities (up to 99% yield and 93% ee). Graphical abstract: Image 1 Highlights: The first organocatalytic asymmetric reaction of hexahydro-1, 3, 5-triazines is reported. We developed a simple and convenient method for generating a new type of spiro-imidazolidinethione-oxindoles.