Dearomatization of 3‐Nitroindoles with Highly γ‐Functionalized Allenoates in Formal (3+2) Cycloadditions

Léo Birbaum; Laurent Gillard; Hélène Gérard; Hassan Oulyadi; Guillaume Vincent; Xavier Moreau; Michaël de Paolis; Isabelle Chataigner

Dearomatization of 3‐Nitroindoles with Highly γ‐Functionalized Allenoates in Formal (3+2) Cycloadditions

Léo Birbaum ¹ Laurent Gillard ¹ Hélène Gérard ² Hassan Oulyadi ¹ Guillaume Vincent ³ Xavier Moreau ⁴ Michaël de Paolis ¹ Isabelle Chataigner ¹

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

2 LCT - Laboratoire de chimie théorique

3 ICMMO - Institut de Chimie Moléculaire et des Matériaux d'Orsay

4 ILV - Institut Lavoisier de Versailles

Abstract : 3‐Nitroindoles are easily reacted with highly substituted γ‐allenoates in the presence of a commercially available phosphine catalyst. For instance, allenoates derived from biomolecules such as amino and deoxycholic acids are combined for the first time with 3‐nitroindole. The corresponding dearomatized (3+2) tricyclic cycloadducts are obtained as α‐regioisomers exclusively. DFT computations shed light on this multi‐step reaction mechanism and on the selectivities observed in the sequence.

Type de document :

Article dans une revue

Domaine :

Chimie

Liste complète des métadonnées

https://hal-normandie-univ.archives-ouvertes.fr/hal-02330833
Contributeur : Madeleine Roux-Merlin <>
Soumis le : jeudi 24 octobre 2019 - 10:46:57
Dernière modification le : jeudi 7 novembre 2019 - 11:38:04

Dearomatization of 3‐Nitroindoles with Highly γ‐Functionalized Allenoates in Formal (3+2) Cycloadditions

Identifiants

Collections

Citation

Exporter

Métriques

10

Dearomatization of 3‐Nitroindoles with Highly γ‐Functionalized Allenoates in Formal (3+2) Cycloadditions

Identifiants

Collections

Citation

Exporter

Partager

Métriques

10