Chiral Atropisomeric‐NHC Catechodithiolate Ruthenium Complexes for <i>Z</i>‐Selective Asymmetric Ring‐Opening Cross Metathesis of <i>Exo</i>‐Norbornenes-Reference-Cited by-同舟云学术

Chiral Atropisomeric‐NHC Catechodithiolate Ruthenium Complexes for Z‐Selective Asymmetric Ring‐Opening Cross Metathesis of Exo‐Norbornenes

Published:2023-04-03 Issue:28 Volume:29 Page:
ISSN:0947-6539
Container-title:Chemistry – A European Journal
language:en
Short-container-title:Chemistry A European J

Author:

Morvan Jennifer¹,Bouëtard Dylan¹,Kong Lingyu²^ORCID,Chou Yajie²,Vives Thomas¹^ORCID,Albalat Muriel²^ORCID,Roisnel Thierry¹^ORCID,Crévisy Christophe¹^ORCID,Nava Paola²^ORCID,Humbel Stéphane²^ORCID,Vanthuyne Nicolas²^ORCID,Clavier Hervé²^ORCID,Mauduit Marc¹^ORCID

Affiliation:

1. Ecole Nationale Supérieure de Chimie de Rennes CNRS ISCR UMR 6226 Univ Rennes 35000 Rennes France

2. Centrale Marseille iSm2 Aix Marseille Univ. CNRS Marseille France

Abstract

AbstractA set of 16 chiral ruthenium complexes containing atropisomerically stable N‐Heterocyclic Carbene (NHC) ligands was synthesized from prochiral NHC precursors. After a rapid screening in asymmetric ring‐opening‐cross metathesis (AROCM), the most effective chiral atropBIAN‐NHC Ru‐catalyst (up to 97 : 3 er) was then converted to a Z‐selective catechodithiolate complex. The latter proved to be highly efficient in Z‐selective AROCM of exo‐norbornenes affording valuable trans‐cyclopentanes with excellent Z‐selectivity (>98 %) and high enantioselectivity (up to 96.5 : 3.5 er).

Funder

Région Bretagne

Agence Nationale de la Recherche

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/chem.202300341

Reference84 articles.

2. Handbook of Metathesis

3. Olefin Metathesis

4. Recent advances in ruthenium-based olefin metathesis

5. Selected book chapter or review see:

Cited by 4 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Ruthenium‐catalyzed asymmetric ene‐yne metathesis;ChemCatChem;2024-01-23

2. An Anthracene-Thiolate-Ligated Ruthenium Complex: Computational Insights into Z-Stereoselective Cross Metathesis;The Journal of Physical Chemistry A;2023-11-02

3. Chirality Transfer Intramolecular Pauson–Khand Reaction with N–C Axially Chiral Sulfonamides Bearing an Ene–Yne Structure;Organic Letters;2023-10-02

4. C ₂-Symmetric atropisomeric N-heterocyclic carbene–palladium(ii) complexes: synthesis, chiral resolution, and application in the enantioselective α-arylation of amides;Dalton Transactions;2023