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

Authors :: Reviriot Y
Michelet B
Beaud R
Martin-Mingot A
Guégan F
Thibaudeau S
Rodriguez J
Bonne D
Source :: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2022 May 02; Vol. 28 (25), pp. e202200432. Date of Electronic Publication: 2022 Mar 28.
Publication Year :: 2022
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.<br /> (© 2022 Wiley-VCH GmbH.)

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