Catalytic [4+2] Cyclization of α,β-Unsaturated Acyl Chlorides with 3-Alkylenyloxindoles: Highly Diastereo- and Enantioselective Synthesis of Spirocarbocyclic Oxindoles†
Dr. Li-Tao Shen
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
Search for more papers by this authorWen-Qiang Jia
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Song Ye
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)Search for more papers by this authorDr. Li-Tao Shen
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
Search for more papers by this authorWen-Qiang Jia
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Song Ye
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)Search for more papers by this authorFinancial support from the Ministry of Science and Technology of China (2011CB808600), National Natural Science Foundation of China (No. 21072195), and the Chinese Academy of Sciences is gratefully acknowledged.
Graphical Abstract
Cinchona alkaloids were used as Lewis base catalysts in the title reaction. The [4+2] cyclization of α,β-unsaturated acyl chlorides with electron-deficient alkenes derived from oxindole gave the corresponding spirocarbocyclic oxindoles.
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