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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
Author(s) -
Reviriot Yasmin,
Michelet Bastien,
Beaud Rodolphe,
MartinMingot Agnès,
Guégan Frédéric,
Thibaudeau Sébastien,
Rodriguez Jean,
Bonne Damien
Publication year - 2022
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202200432
Subject(s) - iminium , intramolecular force , enantioselective synthesis , chemistry , superacid , adduct , stereochemistry , pictet–spengler reaction , ion , organic chemistry , catalysis
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.