Zuschrift
Enantioselective Michael/Mannich Polycyclization Cascade of Indolyl Enones Catalyzed by Quinine-Derived Primary Amines†
Quan Cai,
Chao Zheng,
Jun-Wei Zhang,
Prof. Dr. Shu-Li You,
Quan Cai
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/
Search for more papers by this authorChao Zheng
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/
Search for more papers by this authorJun-Wei Zhang
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/
Search for more papers by this authorCorresponding Author
Prof. Dr. Shu-Li You
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/Search for more papers by this authorQuan Cai,
Chao Zheng,
Jun-Wei Zhang,
Prof. Dr. Shu-Li You,
Quan Cai
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/
Search for more papers by this authorChao Zheng
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/
Search for more papers by this authorJun-Wei Zhang
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/
Search for more papers by this authorCorresponding Author
Prof. Dr. Shu-Li You
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/Search for more papers by this author†
We thank the National Natural Science Foundation of China (20732006, 20821002, 21025209), the National Basic Research Program of China (973 Program 2010CB833300), and the Chinese Academy of Sciences for generous financial support.
Graphical Abstract
Base und Säure bilden zusammen den Katalysator für die Titelreaktion, die diastereoselektiv und hoch enantioselektiv tetracylische Strukturen mit drei Stereozentren liefert (siehe Schema; Ts=4-Toluolsulfonyl). Mit dieser Reaktion wurde das Grundgerüst von (+)-Kreysiginin aufgebaut.
Supporting Information
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- 12The absolute configuration was determined by the X-ray diffraction analysis of enantiopure 3 b. CCDC 808361 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
- 13Since only two diastereoisomers were isolated, the origin of the diastereoselectivity was studied by computational method. The DFT calculations suggested that the Mannich reaction is stereospecific because of the rigid polycylic skeleton. The cis-fused [4.3.0] bicyclic structure is the only accessible product of the cyclization process. See the Supporting Information for details.
- 14The relative configurations of 3 k and 3 k′ were determined by the X-ray diffraction. CCDC 828201 and 828107 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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