Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reaction
Treatment of various (R)-N-(2,2,3,3-tetrafluoropent-4-en-1-ylidene)-1-phenylethylamine derivatives with 2.4 equiv of DBU in toluene at room temperature to 50 °C for 24 h led to a smooth [1,3]-proton shift reaction with a high chirality transfer, affording the corresponding rearranged products in acc...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2024-11-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.20.233 |
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| author | Yuta Kabumoto Eiichiro Yoshimoto Bing Xiaohuan Masato Morita Motohiro Yasui Shigeyuki Yamada Tsutomu Konno |
| author_facet | Yuta Kabumoto Eiichiro Yoshimoto Bing Xiaohuan Masato Morita Motohiro Yasui Shigeyuki Yamada Tsutomu Konno |
| author_sort | Yuta Kabumoto |
| collection | DOAJ |
| description | Treatment of various (R)-N-(2,2,3,3-tetrafluoropent-4-en-1-ylidene)-1-phenylethylamine derivatives with 2.4 equiv of DBU in toluene at room temperature to 50 °C for 24 h led to a smooth [1,3]-proton shift reaction with a high chirality transfer, affording the corresponding rearranged products in acceptable yields. Without purification, these products were subjected to acid hydrolysis and the subsequent N-Cbz protection, providing the optically active tetrafluoroethylenated amides in moderate three-step yields. |
| format | Article |
| id | doaj-art-bfbbe527873f4e67a2e192e9e4387d6b |
| institution | DOAJ |
| issn | 1860-5397 |
| language | English |
| publishDate | 2024-11-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-bfbbe527873f4e67a2e192e9e4387d6b2025-08-20T02:51:15ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972024-11-012012776278310.3762/bjoc.20.2331860-5397-20-233Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reactionYuta Kabumoto0Eiichiro Yoshimoto1Bing Xiaohuan2Masato Morita3Motohiro Yasui4Shigeyuki Yamada5Tsutomu Konno6Faculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan Faculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan Faculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan Department of Materials Science and Engineering, Graduate School of Science and Engineering, Ibaraki University, 4-12-1 Nakanarusawa, Hitachi, Ibaraki 316-8511, Japan Faculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan Faculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan Faculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan Treatment of various (R)-N-(2,2,3,3-tetrafluoropent-4-en-1-ylidene)-1-phenylethylamine derivatives with 2.4 equiv of DBU in toluene at room temperature to 50 °C for 24 h led to a smooth [1,3]-proton shift reaction with a high chirality transfer, affording the corresponding rearranged products in acceptable yields. Without purification, these products were subjected to acid hydrolysis and the subsequent N-Cbz protection, providing the optically active tetrafluoroethylenated amides in moderate three-step yields.https://doi.org/10.3762/bjoc.20.233aminechirality transfer[1,3]-proton shift reactiontetrafluoroethylene fragment |
| spellingShingle | Yuta Kabumoto Eiichiro Yoshimoto Bing Xiaohuan Masato Morita Motohiro Yasui Shigeyuki Yamada Tsutomu Konno Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reaction Beilstein Journal of Organic Chemistry amine chirality transfer [1,3]-proton shift reaction tetrafluoroethylene fragment |
| title | Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reaction |
| title_full | Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reaction |
| title_fullStr | Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reaction |
| title_full_unstemmed | Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reaction |
| title_short | Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reaction |
| title_sort | access to optically active tetrafluoroethylenated amines based on 1 3 proton shift reaction |
| topic | amine chirality transfer [1,3]-proton shift reaction tetrafluoroethylene fragment |
| url | https://doi.org/10.3762/bjoc.20.233 |
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