Nucleophilic addition of 3,3,3-trifluoropropynyllithium to d-glyceraldimine: Concise synthesis of both enantiomers of 5,5,5-trifluoronorvaline |
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| Authors: | Qi Chen Feng-Ling Qing |
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| Affiliation: | a Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 354 Fenglin Lu, Shanghai 200032, China
b Institute of Biological Sciences and Biotechnology, Donghua University, 2999 North Renmin Lu, Shanghai 201620, China |
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| Abstract: | 3,3,3-Trifluoropropynyllithium, in situ generated by treatment of 2-bromo-3,3,3-trifluoro-1-propene 1 with 2.0 equiv. of LDA at −78 °C, was trapped with d-glyceraldimine 2 to give trifluoromethylated propargylic amine 4 in 55% yield. Starting from the key intermediate 4, Boc-protected (R)-5,5,5-trifluoronorvaline and (S)-5,5,5-trifluoronorvaline were concisely synthesized over three steps in 62% and 63% yield, respectively. |
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| Keywords: | Fluorinated amino acids 3,3,3-Trifluoropropynyllithium 5,5,5-Trifluoronorvaline |
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