Access to the Enantiopure Axially Chiral Cyclophane Isoplagiochin D through Atropo-diastereoselective Heck Coupling

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MEIDLINGER, D., MARX, L., BORDEIANU, Catalina, CHOPPIN, Sabine, COLOBERT-LEUENBERGER, Francoise et SPEICHER, A., 2018. Access to the Enantiopure Axially Chiral Cyclophane Isoplagiochin D through Atropo-diastereoselective Heck Coupling. Angewandte Chemie International Edition [en ligne]. 2018. Vol. 57, n° 29pp. 9160-9164. [Consultésans date]. DOI 10.1002/anie.201803677. Consulté de : https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.2018036771. .
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Auteurs D Meidlinger
L Marx
Catalina Bordeianu
Sabine Choppin
Francoise Colobert-leuenberger
A Speicher
Unité de recherche du site Institut de Physique et Chimie des Matériaux de Strasbourg - IPCMS - UMR7504
Laboratoire d'Innovation Moléculaire et Applications - LIMA - UMR7042
Langue

en
Volume

57
Numéro

29
Page de début

9160
Page de fin

9164
Date de première publication

2018
Titre de la source (revue, livre…)

Angewandte Chemie International Edition
Résumé

Macrocyclization is typically the key step in the syntheses of cyclophane-type natural products. Considering cyclophanes with axially chiral biaryl moieties, the control of atroposelectivity is essential with biological activity and is synthetically Show moreMacrocyclization is typically the key step in the syntheses of cyclophane-type natural products. Considering cyclophanes with axially chiral biaryl moieties, the control of atroposelectivity is essential with biological activity and is synthetically challenging. We report an atroposelective approach involving Heck cyclization, which for the first time enables the total synthesis of an enantiopure macrocyclic bis(bibenzyl), namely isoplagiochin D. An enantiopure sulfinyl auxiliary in the ortho position of a biaryl axis (still flexible) was used to induce an atropo-diastereoselective Heck coupling (up to 98 % de). The traceless character of the sulfinyl auxiliary enables the introduction of a hydroxy group to give the target molecule with 98 % ee as well. Show less
DOI 10.1002/anie.201803677
URL éditeur https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201803677
Type de publication

journal article
Type de publication

ACL
Domaine

Chimie/Chimie organique
Mots-clés

SYNCAT
Unité de recherche extérieure au site

Department of Organic Chemistry, Saarland University, Campus C4.2, 66123 Saarbrücken, Germany
Fonction

aut
Identifiant idREF 13980367X
06045654X
Audience

Non spécifiée
Envoyer vers HAL

5
URL https://univoak.eu/islandora/object/islandora:78951