Aza-Payne rearrangement of α,α-disubstituted-aziridinemethanols |
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| Institution: | 1. Department of Chemistry and the Tsinghua Center for Frontier Polymer Research, Tsinghua University, Beijing 100084, China;2. Beijing National Laboratory for Molecular Sciences, Key Laboratory of Polymer Chemistry and Physics of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China;3. PCFM Lab, DSAPM Lab and KLGHEI of Environment and Energy Chemistry, FCM Institute, State Key Laboratory of Optoelectronic Materials and Technologies, School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, China;1. Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India;2. Chemical Biology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India;1. Nofer Institute of Occupational Medicine, Department of Environmental and Biological Monitoring, Lodz, Poland;2. Department of Organic and Applied Chemistry, University of Lodz, Poland;3. Department of Biostatistics and Translational Medicine, Medical University of Lodz, Poland;4. Postgraduate School of Molecular Medicine, Medical University of Warsaw, Poland |
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| Abstract: | The aza-Payne rearrangement of activated N-Ts-α,α-disubstituted-aziridinemethanols, induced by NaOH in the mixed solvent tBuOH/H2O/THF (4:5:1) or NaH in a mixed solvent of THF/HMPA (10:1), as well as some N-Boc-α,α-disubstituted-aziridinemethanols with the latter reagent/solvent combination, provides the corresponding epoxides in up to 99% yield. |
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