Organocatalytic double arylation of 3-isothiocyanato oxindoles: Stereocontrolled synthesis of complex spirooxindoles

Zhang, Lin-Lin1,2; Da, Bing-Chao2; Xiang, Shao-Hua3; Zhu, Shuai2; Yuan, Zi-Yun2; Guo, Zhen1; Tan, Bin2

2019-03-22

10.1016/j.tet.2018.11.016

TETRAHEDRON   影响因子和分区

0040-4020

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. (C) 2018 Elsevier Ltd. All rights reserved.

Organocatalytic Quinones 3-Isothiocyanato oxindoles Pyrrolidonyl spirooxindoles Stereocontrol

SCI ; CPCI-S ; IC ; CCR

英语

通讯

Southern University of Science and Technology[K01211007]

Chemistry

Chemistry, Organic

WOS:000462418900018

PERGAMON-ELSEVIER SCIENCE LTD

CHEMISTRY

Web of Science

1.Taiyuan Univ Technol, Coll Mat Sci & Engn, Taiyuan 030024, Shanxi, Peoples R China
2.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China
3.Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, Shenzhen 518055, Peoples R China

Zhang, Lin-Lin,Da, Bing-Chao,Xiang, Shao-Hua,et al. Organocatalytic double arylation of 3-isothiocyanato oxindoles: Stereocontrolled synthesis of complex spirooxindoles[J]. TETRAHEDRON,2019,75(12):1689-1696.

Zhang, Lin-Lin.,Da, Bing-Chao.,Xiang, Shao-Hua.,Zhu, Shuai.,Yuan, Zi-Yun.,...&Tan, Bin.(2019).Organocatalytic double arylation of 3-isothiocyanato oxindoles: Stereocontrolled synthesis of complex spirooxindoles.TETRAHEDRON,75(12),1689-1696.

Zhang, Lin-Lin,et al."Organocatalytic double arylation of 3-isothiocyanato oxindoles: Stereocontrolled synthesis of complex spirooxindoles".TETRAHEDRON 75.12(2019):1689-1696.