[HCo(CO)4]-Catalyzed Three-component Cycloaddition of Epoxides, Imines, and Carbon Monoxide: Facile Construction of 1,3-Oxazinan-4-ones†
Lixia Liu
State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, and Department of Chemistry, Nankai University, Tianjin, 300071 (P.R. China)
Search for more papers by this authorCorresponding Author
Prof. Huailin Sun
State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, and Department of Chemistry, Nankai University, Tianjin, 300071 (P.R. China)
State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, and Department of Chemistry, Nankai University, Tianjin, 300071 (P.R. China)Search for more papers by this authorLixia Liu
State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, and Department of Chemistry, Nankai University, Tianjin, 300071 (P.R. China)
Search for more papers by this authorCorresponding Author
Prof. Huailin Sun
State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, and Department of Chemistry, Nankai University, Tianjin, 300071 (P.R. China)
State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, and Department of Chemistry, Nankai University, Tianjin, 300071 (P.R. China)Search for more papers by this authorThis work was supported by the NSFC (Project No. 20834002), the Natural Science Foundation of Tianjin (Project No. 08JCZDJC21600), and the Ministry of Education of China (Project No. 03406).
Graphical Abstract
Cobalt and CO: The title reaction is described to proceed in the presence of [HCo(CO)4] as the catalyst. The reaction occurs for a wide variety of imines and various substituted epoxides, thus providing an efficient and atom-economic route to 1,3-oxazinan-4-ones, with various substitution patterns, from simple and readily available starting materials.
Abstract
The three-component [3+2+1] cycloaddition of epoxides, imines, and carbon monoxide to produce 1,3-oxazinan-4-ones has been developed by using [HCo(CO)4] as the catalyst. The reaction occurs for a wide variety of imines and epoxides, under 60 bar of CO pressure at 50 °C, to produce 1,3-oxazinan-4-ones with different substitution patterns in high yields, and provides an efficient and atom-economic route to heterocycles from simple and readily available starting materials. A plausible mechanism involves [HCo(CO)4]-induced ring-opening of the epoxide, followed by sequential addition of carbon monoxide and the imine, and then ring closure to form the product accompanied by regeneration of [HCo(CO)4].
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