Concise Report
Rhodium-Catalyzed Regioselective C—O and C—C Bonds Formation of 3-Oxopent-4-enenitriles with Alkynes for the Synthesis of Polysubstituted 2H-Pyrans
Kelu Yan,
Xiao Liu,
Jiangwei Wen,
Qiuyun Li,
Junjie Wang,
Yang Zheng,
Xiu Wang,
Corresponding Author
Kelu Yan
Key Laboratory of Life-Organic Analysis of Shandong Province, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong, 273165 China
E-mail: [email protected]Search for more papers by this authorXiao Liu
Key Laboratory of Life-Organic Analysis of Shandong Province, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong, 273165 China
Search for more papers by this authorJiangwei Wen
Key Laboratory of Life-Organic Analysis of Shandong Province, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong, 273165 China
Search for more papers by this authorQiuyun Li
Faculty of Chemistry and Chemical Engineering, Yancheng Institute of Technology, Yancheng, Jiangsu, 224051 China
Search for more papers by this authorJunjie Wang
Key Laboratory of Life-Organic Analysis of Shandong Province, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong, 273165 China
Search for more papers by this authorYang Zheng
Key Laboratory of Life-Organic Analysis of Shandong Province, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong, 273165 China
Search for more papers by this authorXiu Wang
Key Laboratory of Life-Organic Analysis of Shandong Province, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong, 273165 China
Search for more papers by this authorKelu Yan,
Xiao Liu,
Jiangwei Wen,
Qiuyun Li,
Junjie Wang,
Yang Zheng,
Xiu Wang,
Corresponding Author
Kelu Yan
Key Laboratory of Life-Organic Analysis of Shandong Province, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong, 273165 China
E-mail: [email protected]Search for more papers by this authorXiao Liu
Key Laboratory of Life-Organic Analysis of Shandong Province, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong, 273165 China
Search for more papers by this authorJiangwei Wen
Key Laboratory of Life-Organic Analysis of Shandong Province, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong, 273165 China
Search for more papers by this authorQiuyun Li
Faculty of Chemistry and Chemical Engineering, Yancheng Institute of Technology, Yancheng, Jiangsu, 224051 China
Search for more papers by this authorJunjie Wang
Key Laboratory of Life-Organic Analysis of Shandong Province, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong, 273165 China
Search for more papers by this authorYang Zheng
Key Laboratory of Life-Organic Analysis of Shandong Province, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong, 273165 China
Search for more papers by this authorXiu Wang
Key Laboratory of Life-Organic Analysis of Shandong Province, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong, 273165 China
Search for more papers by this authorComprehensive Summary
The rhodium-catalyzed C—H bond activation and cyclization of 3-oxopent-4-enenitriles with alkynes proceed efficiently. Various 2H-pyrans with multiple substituents are achieved in good yields through regioselective formation of C—O and C—C bonds. Transformations involving hydroxy-alkynoates resulted in products with a furo[3,4-b]pyran skeleton via further intramolecular ester exchange processes. Different from the traditional “1-oxatrienes pathway”, this method for the synthesis of useful 2H-pyrans possesses certain highlights in terms of readily available substrates, stable and easily derivatized products, gentle and convenient operation process, and step and atom economy.
Supporting Information
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Appendix S1: Supporting Information |
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