Eu(OTf)3-Catalyzed Formal Dipolar [4π+2σ] Cycloaddition of Bicyclo-[1.1.0]butanes with Nitrones: Access to Polysubstituted 2-Oxa-3-azabicyclo[3.1.1]heptanes
Corresponding Author
Dr. Jian Zhang
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, 688 Yingbin Road, Jinhua, 321004 China
Search for more papers by this authorJia-Yi Su
State Key Laboratory of Bioreactor Engineering, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
Search for more papers by this authorDr. Hanliang Zheng
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, 688 Yingbin Road, Jinhua, 321004 China
Search for more papers by this authorProf. Dr. Hao Li
State Key Laboratory of Bioreactor Engineering, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Wei-Ping Deng
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, 688 Yingbin Road, Jinhua, 321004 China
Search for more papers by this authorCorresponding Author
Dr. Jian Zhang
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, 688 Yingbin Road, Jinhua, 321004 China
Search for more papers by this authorJia-Yi Su
State Key Laboratory of Bioreactor Engineering, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
Search for more papers by this authorDr. Hanliang Zheng
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, 688 Yingbin Road, Jinhua, 321004 China
Search for more papers by this authorProf. Dr. Hao Li
State Key Laboratory of Bioreactor Engineering, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Wei-Ping Deng
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, 688 Yingbin Road, Jinhua, 321004 China
Search for more papers by this authorGraphical Abstract
Rapid access of diverse polysubstituted 2-oxa-3-azabicyclo[3.1.1]heptanes, which were not readily accessible by known methods, has been realized through Eu(OTf)3-catalyzed formal dipolar [4π+2σ] cycloaddition of bicyclo[1.1.0]butanes with easily accessible nitrones.
Abstract
Herein, we have synthesized multifunctionalized 2-oxa-3-azabicyclo[3.1.1]heptanes, which are considered potential bioisosteres for meta-substituted arenes, through Eu(OTf)3-catalyzed formal dipolar [4π+2σ] cycloaddition of bicyclo[1.1.0]butanes with nitrones. This methodology represents the initial instance of fabricating bicyclo[3.1.1]heptanes adorned with multiple heteroatoms. The protocol exhibits both mild reaction conditions and a good tolerance for various functional groups. Computational density functional theory calculations support that the reaction mechanism likely involves a nucleophilic addition of nitrones to bicyclo[1.1.0]butanes, succeeded by an intramolecular cyclization. The synthetic utility of this novel protocol has been demonstrated in the concise synthesis of the analogue of Rupatadine.
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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