Organocatalytic Diastereo- and Enantioselective 1,3-Dipolar Cycloaddition of Azlactones and Methyleneindolinones†
Wangsheng Sun
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)
These authors contributed equally.
Search for more papers by this authorGongming Zhu
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)
These authors contributed equally.
Search for more papers by this authorChongyang Wu
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)
Search for more papers by this authorGuofeng Li
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)
Search for more papers by this authorCorresponding Author
Dr. Liang Hong
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)Search for more papers by this authorCorresponding Author
Prof. Dr. Rui Wang
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)Search for more papers by this authorWangsheng Sun
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)
These authors contributed equally.
Search for more papers by this authorGongming Zhu
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)
These authors contributed equally.
Search for more papers by this authorChongyang Wu
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)
Search for more papers by this authorGuofeng Li
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)
Search for more papers by this authorCorresponding Author
Dr. Liang Hong
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)Search for more papers by this authorCorresponding Author
Prof. Dr. Rui Wang
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000 (P.R. China)Search for more papers by this authorWe gratefully acknowledge financial support from the NSFC (20932003, 91213302, 21272102, 21202071) and the National S&T Major Project of China (2012ZX09504001-003). W.S. is grateful for a Scholarship Award for Distinguished Doctoral Candidates granted by the Ministry of Education, China.
Graphical Abstract
A simple route to complexity: An organocatalytic 1,3-dipolar cycloaddition between azlactones and methyleneindolinones provided spirooxindoles with high enantioselectivity (see scheme). This transformation takes advantage of the nucleophilic C4 and electrophilic C2 atoms in the azlactone substrate. Bn=benzyl, HOBt=1-hydroxy-1H-benzotriazole, MTBE=methyl tert-butyl ether, PG=protecting group, TMS=trimethylsilyl.
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