Hidden Heptacyclic Chiral  N ‐Acyl Iminium Ions: A New Entry to Enantioenriched Polycyclic Azepanes and Azocanes by Superacid‐Promoted Intramolecular Pictet‐Spengler Reaction | Zendy

Reviriot Yasmin | Zendy; Michelet Bastien | Zendy; Beaud Rodolphe | Zendy; MartinMingot Agnès | Zendy; Guégan Frédéric | Zendy; Thibaudeau Sébastien | Zendy; Rodriguez Jean | Zendy; Bonne Damien | Zendy

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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.

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