Issue 18, 2022
From the journal:

Chemical Communications

Synthesis of chiral polycyclic N-heterocycles via gold(i)-catalyzed 1,6-enyne cyclization/intramolecular nucleophilic addition†

Xu Han,ab   Quentin Gaignard-Gaillard,ab   Pascal Retailleau,a   Vincent Gandon ORCID logo *bc  and  Arnaud Voituriez ORCID logo *a  

* Corresponding authors

a Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, Gif-sur-Yvette, France
E-mail: arnaud.voituriez@cnrs.fr

b Université Paris-Saclay, CNRS, Institut de Chimie Moléculaire et des Matériaux d’Orsay, Orsay, France
E-mail: vincent.gandon@universite-paris-saclay.fr

c Laboratoire de Chimie Moléculaire (LCM), CNRS UMR 9168, Ecole Polytechnique, Institut Polytechnique de Paris, route de Saclay, 91128 Palaiseau cedex, France

Abstract

Cycloisomerization of N-tethered indole- and dihydropyrrole-arylpropargyl substrates into complex polycycles was investigated by using gold(I) catalysis. Enantioselectivities up to 93% ee were obtained in the asymmetric version of this process. DFT calculations rationalized the reactivity observed for the formation of such complex molecular frameworks.

Graphical abstract: Synthesis of chiral polycyclic N-heterocycles via gold(i)-catalyzed 1,6-enyne cyclization/intramolecular nucleophilic addition

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Article information

DOI
https://doi.org/10.1039/D1CC06388J
Article type
Communication
Submitted
12 Nov 2021
Accepted
25 Jan 2022
First published
25 Jan 2022

Chem. Commun., 2022,58, 3043-3046

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Synthesis of chiral polycyclic N-heterocycles via gold(I)-catalyzed 1,6-enyne cyclization/intramolecular nucleophilic addition

X. Han, Q. Gaignard-Gaillard, P. Retailleau, V. Gandon and A. Voituriez, Chem. Commun., 2022, 58, 3043 DOI: 10.1039/D1CC06388J

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