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A highly diastereo- and enantioselective synthesis of tetrahydroquinolines: quaternary stereogenic center inversion and functionalization.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Luo, Chaosheng Huang, Yawen |
| Copyright Year | 2013 |
| Abstract | Tetrahydroquinolines containing two quaternary stereogenic centers were synthesized with excellent ee and dr via a four-component cyclization reaction catalyzed by a chiral phosphoric acid. High chemoselectivity was achieved by differentiating anilines with similar reactivities to yield diverse "hybrid" products. The chirality of the quaternary C4 atom of the 4-aminotetrahydroquinoline products was found to undergo highly stereoselective inversion, enabling facile functionalization using a wide range of nucleophiles (C, O, N, and S). |
| File Format | PDF HTM / HTML |
| DOI | 10.1021/ja4040945 |
| PubMed reference number | 23676113 |
| Journal | Medline |
| Volume Number | 135 |
| Issue Number | 22 |
| Alternate Webpage(s) | http://web.pkusz.edu.cn/huang/files/2013/04/A-Highly-Diastereo-and-Enantioselective-Synthesis-of-Tetrahydroquinolines-Quaternary-Stereogenic-Center-Inversion-and-Functionalization.pdf |
| Alternate Webpage(s) | https://doi.org/10.1021/ja4040945 |
| Journal | Journal of the American Chemical Society |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |