Organocatalytic double arylation of 3-isothiocyanato oxindoles: Stereocontrolled synthesis of complex spirooxindoles. Issue 12 (22nd March 2019)

• Record Type: Journal Article
• Authors: Zhang, Lin-Lin; Da, Bing-Chao; Xiang, Shao-Hua; Zhu, Shuai; Yuan, Zi-Yun; Guo, Zhen; Tan, Bin
• Is Part Of: Tetrahedron. Volume 75:Issue 12(2019)
• Page Start: 1689
• Page End: 1696
• Publication Date: 2019-03-22
• Subjects: Organocatalytic -- Quinones -- 3-Isothiocyanato oxindoles -- Pyrrolidonyl spirooxindoles -- Stereocontrol; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.11.016
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Quinones, precursors of aromatic structures, were firstly employed as the electrophiles for the organocatalytic Michael addition/cyclization cascade reaction with versatile 3-isothiocyanato oxindoles. Chiral bifunctional organocatalyst was appropriate for this enantioselective transformation to afford a variety of novel spirooxindoles, possessing a spirocyclic stereocenter adjacent to the aromatic ring, via asymmetric double arylation. These synthesized spirooxindoles are very difficult to access by the reported methods and were obtained in excellent chemical yields with excellent enantioselectivities. Graphical abstract: Image 1