Helical Chiral N‐Heterocyclic Carbene Ligands in Enantioselective Gold Catalysis
Abstract The first chiral helicene‐NHC gold(I) complexes efficient in enantioselective catalysis were prepared. The L‐shaped chiral ligand is composed of an imidazo[1,5‐ a ]pyridin‐3‐ylidene (IPy) scaffold laterally substituted by a configurationally stable [5]‐helicenoid unit. The chiral informatio...
Published in: | Chemistry – A European Journal |
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2022
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Online Access: | http://dx.doi.org/10.1002/chem.202200166 https://onlinelibrary.wiley.com/doi/pdf/10.1002/chem.202200166 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/chem.202200166 https://chemistry-europe.onlinelibrary.wiley.com/doi/am-pdf/10.1002/chem.202200166 |
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crwiley:10.1002/chem.202200166 2024-09-09T19:48:26+00:00 Helical Chiral N‐Heterocyclic Carbene Ligands in Enantioselective Gold Catalysis Pallova, Lenka Abella, Laura Jean, Marion Vanthuyne, Nicolas Barthes, Cécile Vendier, Laure Autschbach, Jochen Crassous, Jeanne Bastin, Stéphanie César, Vincent Agence Nationale de la Recherche National Science Foundation 2022 http://dx.doi.org/10.1002/chem.202200166 https://onlinelibrary.wiley.com/doi/pdf/10.1002/chem.202200166 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/chem.202200166 https://chemistry-europe.onlinelibrary.wiley.com/doi/am-pdf/10.1002/chem.202200166 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#am http://onlinelibrary.wiley.com/termsAndConditions#vor Chemistry – A European Journal volume 28, issue 17 ISSN 0947-6539 1521-3765 journal-article 2022 crwiley https://doi.org/10.1002/chem.202200166 2024-06-20T04:24:26Z Abstract The first chiral helicene‐NHC gold(I) complexes efficient in enantioselective catalysis were prepared. The L‐shaped chiral ligand is composed of an imidazo[1,5‐ a ]pyridin‐3‐ylidene (IPy) scaffold laterally substituted by a configurationally stable [5]‐helicenoid unit. The chiral information was introduced in a key post‐functionalization step of a NHC‐gold(I) complex bearing a symmetrical anionic fluoreno[5]helicene substituent, leading to a racemic mixture of complexes featuring three correlated elements of chirality, namely central, axial and helical chirality. After HPLC enantiomeric resolution, X‐ray crystallography and theoretical calculations enabled structural and stereochemical characterization of these configurationally stable NHC‐gold(I) complexes. The high potential in asymmetric catalysis is demonstrated in the benchmark cycloisomerization of N‐tethered 1,6‐enynes with up to 95 : 5 er. Article in Journal/Newspaper IPY Wiley Online Library Chemistry – A European Journal 28 17 |
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Wiley Online Library |
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crwiley |
language |
English |
description |
Abstract The first chiral helicene‐NHC gold(I) complexes efficient in enantioselective catalysis were prepared. The L‐shaped chiral ligand is composed of an imidazo[1,5‐ a ]pyridin‐3‐ylidene (IPy) scaffold laterally substituted by a configurationally stable [5]‐helicenoid unit. The chiral information was introduced in a key post‐functionalization step of a NHC‐gold(I) complex bearing a symmetrical anionic fluoreno[5]helicene substituent, leading to a racemic mixture of complexes featuring three correlated elements of chirality, namely central, axial and helical chirality. After HPLC enantiomeric resolution, X‐ray crystallography and theoretical calculations enabled structural and stereochemical characterization of these configurationally stable NHC‐gold(I) complexes. The high potential in asymmetric catalysis is demonstrated in the benchmark cycloisomerization of N‐tethered 1,6‐enynes with up to 95 : 5 er. |
author2 |
Agence Nationale de la Recherche National Science Foundation |
format |
Article in Journal/Newspaper |
author |
Pallova, Lenka Abella, Laura Jean, Marion Vanthuyne, Nicolas Barthes, Cécile Vendier, Laure Autschbach, Jochen Crassous, Jeanne Bastin, Stéphanie César, Vincent |
spellingShingle |
Pallova, Lenka Abella, Laura Jean, Marion Vanthuyne, Nicolas Barthes, Cécile Vendier, Laure Autschbach, Jochen Crassous, Jeanne Bastin, Stéphanie César, Vincent Helical Chiral N‐Heterocyclic Carbene Ligands in Enantioselective Gold Catalysis |
author_facet |
Pallova, Lenka Abella, Laura Jean, Marion Vanthuyne, Nicolas Barthes, Cécile Vendier, Laure Autschbach, Jochen Crassous, Jeanne Bastin, Stéphanie César, Vincent |
author_sort |
Pallova, Lenka |
title |
Helical Chiral N‐Heterocyclic Carbene Ligands in Enantioselective Gold Catalysis |
title_short |
Helical Chiral N‐Heterocyclic Carbene Ligands in Enantioselective Gold Catalysis |
title_full |
Helical Chiral N‐Heterocyclic Carbene Ligands in Enantioselective Gold Catalysis |
title_fullStr |
Helical Chiral N‐Heterocyclic Carbene Ligands in Enantioselective Gold Catalysis |
title_full_unstemmed |
Helical Chiral N‐Heterocyclic Carbene Ligands in Enantioselective Gold Catalysis |
title_sort |
helical chiral n‐heterocyclic carbene ligands in enantioselective gold catalysis |
publisher |
Wiley |
publishDate |
2022 |
url |
http://dx.doi.org/10.1002/chem.202200166 https://onlinelibrary.wiley.com/doi/pdf/10.1002/chem.202200166 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/chem.202200166 https://chemistry-europe.onlinelibrary.wiley.com/doi/am-pdf/10.1002/chem.202200166 |
genre |
IPY |
genre_facet |
IPY |
op_source |
Chemistry – A European Journal volume 28, issue 17 ISSN 0947-6539 1521-3765 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#am http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/chem.202200166 |
container_title |
Chemistry – A European Journal |
container_volume |
28 |
container_issue |
17 |
_version_ |
1809917721716981760 |