Organocatalytic double arylation of 3-isothiocyanato oxindoles: Stereocontrolled synthesis of complex spirooxindoles |
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| Authors: | Lin-Lin Zhang Bing-Chao Da Shao-Hua Xiang Shuai Zhu Zi-Yun Yuan Zhen Guo Bin Tan |
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| Institution: | 1. College of Material Science & Engineering, Taiyuan University of Technology, Shanxi 030024, China;2. Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China;3. Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology, Shenzhen 518055, China |
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| 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. |
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| Keywords: | Organocatalytic Quinones 3-Isothiocyanato oxindoles Pyrrolidonyl spirooxindoles Stereocontrol |
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