Tandem InCl3-Promoted Hydroperoxide Rearrangements and Nucleophilic Additions: A Straightforward Entry to Benzoxacycles - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2023

Tandem InCl3-Promoted Hydroperoxide Rearrangements and Nucleophilic Additions: A Straightforward Entry to Benzoxacycles

Résumé

The acid-catalyzed rearrangement of organic peroxides is generally associated with C–C-bond cleavages (Hock and Criegee rearrangements), with the concomitant formation of an oxocarbenium intermediate. This article describes the tandem process between a Hock or Criegee oxidative cleavage and a nucleophilic addition onto the oxocarbenium species (in particular a Hosomi–Sakurai-type allylation), under InCl3 catalysis. It was applied to the synthesis of 2-substituted benzoxacycles (chromanes and benzoxepanes), including a synthesis of the 2-(aminomethyl)chromane part of sarizotan, and a total synthesis of erythrococcamide B.

Domaines

Chimie organique
Fichier principal
Vignette du fichier
postprint.pdf (1.03 Mo) Télécharger le fichier
Origine : Fichiers produits par l'(les) auteur(s)
Licence : CC BY - Paternité

Dates et versions

hal-04239627 , version 1 (15-11-2023)

Identifiants

Citer

Alexandra Bosnidou, Agathe Fayet, Cristina Cheibas, Oscar Gayraud, Sophie Bourcier, et al.. Tandem InCl3-Promoted Hydroperoxide Rearrangements and Nucleophilic Additions: A Straightforward Entry to Benzoxacycles. Journal of Organic Chemistry, 2023, 88 (13), pp.9277-9282. ⟨10.1021/acs.joc.3c00845⟩. ⟨hal-04239627⟩
54 Consultations
2 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More