Enantioselective Construction of Eight-Membered N-Heterocycles from Simple 1,3-Dienes via Pd(0) Lewis Base Catalysis
Jiaoting Pan
Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University Binhai New City, Fuzhou, 350207 China
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Singapore
Search for more papers by this authorTakumi Ogawa Ho
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Singapore
Search for more papers by this authorCorresponding Author
Prof. Ying-Chun Chen
Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu, 610041 P. R. China
Search for more papers by this authorCorresponding Author
Dr. Bin-Miao Yang
Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University Binhai New City, Fuzhou, 350207 China
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Prof. Yu Zhao
Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University Binhai New City, Fuzhou, 350207 China
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Singapore
Search for more papers by this authorJiaoting Pan
Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University Binhai New City, Fuzhou, 350207 China
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Singapore
Search for more papers by this authorTakumi Ogawa Ho
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Singapore
Search for more papers by this authorCorresponding Author
Prof. Ying-Chun Chen
Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu, 610041 P. R. China
Search for more papers by this authorCorresponding Author
Dr. Bin-Miao Yang
Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University Binhai New City, Fuzhou, 350207 China
Search for more papers by this authorCorresponding Author
Prof. Yu Zhao
Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University Binhai New City, Fuzhou, 350207 China
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543 Singapore
Search for more papers by this authorAbstract
We report herein an unprecedented enantioselective (4+4) cycloaddition of simple 1,3-dienes with azadienes for the construction of fused eight-membered N-heterocycles. In this transformation, the π-Lewis basic Pd(0) catalyst achieves activation of 1,3-dienes to induce nucleophilic addition to azadienes followed by ring cyclization via a selective terminal allylic substitution. Furthermore, highly efficient and diastereoselective derivatizations of the eight-membered rings provide a facile access to diverse enantiopure fused tetra- to hexacyclic compounds with potential application in medicinal chemistry.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.
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| ange202317703-sup-0001-rac-11b.cif7.5 MB | Supporting Information |
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