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Hidden Heptacyclic Chiral N-Acyl Iminium Ions: A New Entry to Enantioenriched Polycyclic Azepanes and Azocanes by Superacid-Promoted Intramolecular Pictet-Spengler Reaction |
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| Authors: | Dr. Yasmin Reviriot Dr. Bastien Michelet Dr. Rodolphe Beaud Dr. Agnès Martin-Mingot Dr. Frédéric Guégan Prof. Sébastien Thibaudeau Prof. Jean Rodriguez Dr. Damien Bonne |
| Affiliation: | 1. Aix Marseille Université, CNRS, Centrale Marseille, iSm2 Marseille, Marseille, France;2. Université de Poitiers, UMR-CNRS 7285, IC2MP, 4 rue Michel Brunet, TSA 51106, 86073 Poitiers Cedex 9, France |
| Abstract: | Enantioenriched complex fused-tricyclic azepanes or bridged-polycyclic azocanes were constructed via a two-step sequence involving an enantioselective organocascade followed by superacid activation of the domino adduct. The activated oxa-bridged azepane acts as a key hidden heptacyclic chiral N-acyl iminium ion triggering a chemo- and diastereoselective intramolecular mono- or di-arylation. |
| Keywords: | azocane azepane N-acyliminium ion organocatalysis superacid |