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Intramolecular asymmetric reductive amination: synthesis of enantioenriched dibenz[c,e]azepines† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c8sc04482a
| Content Provider | Semantic Scholar |
|---|---|
| Author | Yang, Tao Guo, Xiaochong Zhang, Xumu |
| Copyright Year | 2019 |
| Abstract | An Ir-catalyzed intramolecular asymmetric reductive amination (ARA) of bridged biaryl derivatives has been described. Using this unprecedented approach, synthetically useful dibenz[c,e]azepines containing both central and axial chiralities are obtained with excellent enantiocontrol (up to 97% ee). This methodology represents a rare example of enantioselective chemocatalytic synthesis of chiral dibenz[c,e]azepines featuring a broad substrate scope, and their synthetic utilities are exhibited by derivatizing the products into a chiral amino acid derivative and chiral phosphoramidite ligands, which display excellent enantiocontrol in Rh-catalyzed asymmetric hydrogenation of α-dehydroamino acid derivatives. Remarkably, our method is also applicable to enantioselectively synthesize an allocolchicine analogue. |
| Starting Page | 2473 |
| Ending Page | 2477 |
| Page Count | 5 |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/c8sc04482a |
| Alternate Webpage(s) | http://www.rsc.org/suppdata/c8/sc/c8sc04482a/c8sc04482a1.pdf |
| Alternate Webpage(s) | https://ftp.ncbi.nlm.nih.gov/pub/pmc/oa_pdf/9e/32/SC-010-C8SC04482A.PMC6385856.pdf |
| Alternate Webpage(s) | https://pubs.rsc.org/en/content/articlepdf/2019/sc/c8sc04482a |
| PubMed reference number | 30881676 |
| Alternate Webpage(s) | https://doi.org/10.1039/c8sc04482a |
| Journal | Medline |
| Volume Number | 10 |
| Journal | Chemical science |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |