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

被引：3

作者：

Reviriot, Yasmin ^{[1
]}

Michelet, Bastien ^{[2
]}

Beaud, Rodolphe ^{[1
]}

Martin-Mingot, Agnes ^{[2
]}

Guegan, Frederic ^{[2
]}

Thibaudeau, Sebastien ^{[2
]}

Rodriguez, Jean ^{[1
]}

Bonne, Damien ^{[1
]}

机构：

[1] Aix Marseille Univ, CNRS, Cent Marseille, iSm2 Marseille, Marseille, France

[2] Univ Poitiers, UMR CNRS 7285, IC2MP, 4 Rue Michel Brunet,TSA 51106, F-86073 Poitiers 9, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2022年 / 28卷 / 25期

关键词：

azocane; azepane; N-acyliminium ion; organocatalysis; superacid; CYCLIZATION; ALKALOIDS; RULES;

D O I：

10.1002/chem.202200432

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页数：6

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