Cycloadditions between methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate and various tosylacetamides: Synthesis of trifluoromethylated pyroglutamates and 2-pyridones derivatives |
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| Authors: | Hong-Hai Zhang Wei Shen Long Lu |
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| Institution: | 1. Key Laborabory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Jiangsu National Synergistic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University (Nanjing Tech), 30 Puzhu Road, Nanjing 211816, PR China;2. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, PR China |
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| Abstract: | Cycloaddition reactions between methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate and various 2-tosylacetamides are described. Various 2-tosylacetamides react with methyl (Z)-2-bromo-4,4,4-trifluoro-2-butenoate in the presence of NaH at room temperature in one step to form trifluoromethylated pyroglutamates as single diastereomers. However, employing the same reactants using t-BuOK as base at ?78?°C results in the formation of trifluoromethylated 2-pyridones. A ring-closure mechanism is proposed for the reaction. |
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| Keywords: | Fluorinated building block Cycloaddition Trifluoromethylated proglutamate Trifluoromethylated dihydropyridine |
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