Dual Cu/Ir Catalyzed Asymmetric Allylation and Pictet-Spengler Cyclization: Stereodivergent Access to Chiral Indole Fused 9-Azabicyclo[4.2.1]nonanes†
Xin-Lian Liu
Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China
Search for more papers by this authorLu Xiao
Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China
Search for more papers by this authorYi Liu
Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China
Search for more papers by this authorYan Li
Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China
Search for more papers by this authorZuo-Fei Wang
Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China
Search for more papers by this authorXin Chang
Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China
Search for more papers by this authorCorresponding Author
Xiu-Qin Dong
Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Chun-Jiang Wang
Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 230021 China
E-mail: [email protected]; [email protected]Search for more papers by this authorXin-Lian Liu
Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China
Search for more papers by this authorLu Xiao
Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China
Search for more papers by this authorYi Liu
Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China
Search for more papers by this authorYan Li
Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China
Search for more papers by this authorZuo-Fei Wang
Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China
Search for more papers by this authorXin Chang
Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China
Search for more papers by this authorCorresponding Author
Xiu-Qin Dong
Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Chun-Jiang Wang
Hubei Research Center of Fundamental Science-Chemistry, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072 China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 230021 China
E-mail: [email protected]; [email protected]Search for more papers by this author† Dedicated to the Special Issue of Catalytic Alkene Functionalization.
Comprehensive Summary
Nitrogen-containing bridged-heterocycles and indoles are key subunits of many natural products and pharmacologically active molecules. We herein present a bimetallic Cu/Ir catalyzed asymmetric allylation of ketimine esters and (E)-4-indolyl allyl carbonates followed by acid-promoted Pictet-Spengler cyclization sequences, enabling stereodivergent synthesis of chiral indole fused 9-azabicyclo[4.2.1]nonanes containing an eight-membered ring with one tertiary and two quaternary stereogenic centers. This one-pot sequential protocol features step economy, good substrate tolerance, and excellent stereoselective control.
Supporting Information
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Appendix S1: Supporting Information |
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