Oxidative kinetic resolution of heterocyclic sulfoxides with a porphyrin-inspired manganese complex by hydrogen peroxide |
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Authors: | Jinchuang Yang Lianyue Wang Ying Lv Ning Li Yue An Shuang Gao |
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Institution: | 1. College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, China;2. Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China;3. College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, Henan, China |
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Abstract: | We have successfully reported here the low loading porphyrin-inspired high-valent manganese (IV)-oxo complex was applied in oxidative kinetic resolution (OKR) of racemic heterocyclic sulfoxides using the environmentally benign hydrogen peroxide for the first time. This approach allows for rapid OKR (0.5?h) of a variety of racemic sulfoxides (including pyridine, pyrimidine, pyrazine, thiazole, benzothiazole, thiophene) in excellent enantioselectivity (up to?>?99%?ee), simultaneously generating the corresponding sulfones in high yield (up to 80%). The catalytic system also showed an unexceptionable chemoselectivity for the sulfoxide substrates with hydroxyl groups in which only the sulfoxide group was oxidized. The practical utility of the method has been demonstrated in the OKR of gram-scale sulfoxides. |
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Keywords: | Oxidative kinetic resolution Heterocyclic sulfoxides Manganese Porphyrin-inspired Sulfone |
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