Catalytic Enantioselective Synthesis of 4-Amino-5-aryltetrahydro-1H-benzo[c]azepines by an Aminoarylation Reaction
| Autor: | Saumen Hajra, Sk Md Samim Akhtar |
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| Rok vydání: | 2022 |
| Předmět: | |
| Zdroj: | Synlett. 34:645-650 |
| ISSN: | 1437-2096 0936-5214 |
| DOI: | 10.1055/a-1912-3285 |
| Popis: | A one-pot asymmetric aminoarylation reaction has been executed for the synthesis of trans-4-amino-5-aryltetrahydrobenzo[c]azepines with excellent diastereo- and enantioselectivity (dr > 99: 1; ee ≤97%). The reaction progresses through aziridination of prochiral N-tosyl-N-cinnamylbenzylamines, followed by an intramolecular 7-endo-tet Friedel–Crafts cyclization of the tethered aziridines generated in situ, where the combination of Cu(OTf)2 as a catalyst and PhINNs as a nitrene source was found to be effective. A chiral indenyl bis(oxazoline) was shown to be an efficient ligand for the catalytic enantioselective version of this one-pot transformation. This 7-endo-tet cyclization is contrary to the Baldwin cyclization rules. |
| Databáze: | OpenAIRE |
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