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Highly efficient construction of chiral dispirocyclic oxindole/thiobutyrolactam/chromanone complexes through Michael/cyclization cascade reactions with a rosin-based squaramide catalyst |
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| Authors: | Ning Lin Xian-wen Long Qing Chen Wen-run Zhu Bi-chuan Wang Kai-bin Chen Cai-wu Jiang Jiang Weng Gui Lu |
| Institution: | 1. College of Pharmacy, Guangxi University of Chinese Medicine, Nanning, Guangxi, 530200, PR China;2. Institute of Medicinal Chemistry, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong, 510006, PR China;3. Guangxi Zhuang Yao Medicine Center of Engineering and Technology, Nanning, Guangxi, 530200, PR China |
| Abstract: | An efficient asymmetric Michael/cyclization cascade reaction of 4-chromanones with isothiocyanato oxindoles has been revealed. Under bifunctional organocatalysis by rosin-based squaramide catalyst, a series of spirooxindole/thiobutyrolactam/chromanone] complexes were conveniently constructed in a highly stereoselective manner (up to 99% yields, > 20:1 dr and >99% ee). The reaction leads to the formation of three contiguous stereogenic centers and two spiro quaternary stereocenters. |
| Keywords: | 3-Isothiocyanato oxindoles Chromanones Dispirocyclic oxindoles Asymmetric organocatalysis Rosin-based squaramide catalyst |
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