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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| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2024-11-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.20.233 |
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| Summary: | 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. |
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| ISSN: | 1860-5397 |