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Copper-Catalyzed Formal Carbene Migratory Insertion into Internal Olefinic C═C Bonds with N-Tosylhydrazones To Access Iminofuran and 2(3H)-Furanone Derivatives.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Huang, Fei Liu, Zhuqing Wang, Quannan Lou, Jiang Yu, Zhengkun |
| Copyright Year | 2017 |
| Abstract | Efficient copper-catalyzed formal carbene migratory insertion into the olefinic C═C bonds of internal olefins, that is, α-oxo ketene N,S-acetals, has been achieved by means of N-tosylhydrazones of ketones as the carbene precursors. Iminofuran derivatives were obtained and further transformed to the corresponding 2(3H)-furanones and 4-oxobutanoates (γ-ketoesters), respectively, under mild conditions. In a similar fashion, α-thioxo ketene N,S-acetals reacted with N-tosylhydrazones of ketones to afford iminothiophenes. It is suggested that formal carbene migratory insertion into the olefinic C═C bond is involved in the overall catalytic cycle, demonstrating a new type of carbene insertion reaction for five-membered heterocycle construction. |
| Starting Page | 3660 |
| Ending Page | 3663 |
| Page Count | 4 |
| File Format | PDF HTM / HTML |
| PubMed reference number | 28613911 |
| Journal | Medline |
| Volume Number | 19 |
| Issue Number | 13 |
| Alternate Webpage(s) | http://www.omcat.dicp.ac.cn/pdf/144_ol-2017.pdf |
| Alternate Webpage(s) | https://doi.org/10.1021/acs.orglett.7b01668 |
| Journal | Organic letters |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
