Enantioselective Synthesis of 1‐Aryl Benzo[5]helicenes Using BINOL‐Derived Cationic Phosphonites as Ancillary Ligands

The synthesis of unprecedented BINOL‐derived cationic phosphonites is described. Through the use of these phosphanes as ancillary ligands in Au(I) catalysis, a highly regio‐ and enantioselective assembly of appropriately designed alkynes into 1‐(aryl)benzo[5]carbohelicenes is achieved. The modular s...

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Autores principales: Redero, Pablo, Hartung, Thierry, Zhang, Jianwei, Nicholls, Leo D. M., Zichen, Guo, Simon, Martin, Golz, Christopher, Alcarazo, Manuel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7756570/
https://www.ncbi.nlm.nih.gov/pubmed/32896999
http://dx.doi.org/10.1002/anie.202010021
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author Redero, Pablo
Hartung, Thierry
Zhang, Jianwei
Nicholls, Leo D. M.
Zichen, Guo
Simon, Martin
Golz, Christopher
Alcarazo, Manuel
author_facet Redero, Pablo
Hartung, Thierry
Zhang, Jianwei
Nicholls, Leo D. M.
Zichen, Guo
Simon, Martin
Golz, Christopher
Alcarazo, Manuel
author_sort Redero, Pablo
collection PubMed
description The synthesis of unprecedented BINOL‐derived cationic phosphonites is described. Through the use of these phosphanes as ancillary ligands in Au(I) catalysis, a highly regio‐ and enantioselective assembly of appropriately designed alkynes into 1‐(aryl)benzo[5]carbohelicenes is achieved. The modular synthesis of these ligands and the enhanced reactivity that they impart to Au(I)‐centers after coordination have been found to be the key features that allow an optimization of the reaction conditions until the desired benzo[5]helicenes are obtained with high yield and enantioselectivity.
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spelling pubmed-77565702020-12-28 Enantioselective Synthesis of 1‐Aryl Benzo[5]helicenes Using BINOL‐Derived Cationic Phosphonites as Ancillary Ligands Redero, Pablo Hartung, Thierry Zhang, Jianwei Nicholls, Leo D. M. Zichen, Guo Simon, Martin Golz, Christopher Alcarazo, Manuel Angew Chem Int Ed Engl Communications The synthesis of unprecedented BINOL‐derived cationic phosphonites is described. Through the use of these phosphanes as ancillary ligands in Au(I) catalysis, a highly regio‐ and enantioselective assembly of appropriately designed alkynes into 1‐(aryl)benzo[5]carbohelicenes is achieved. The modular synthesis of these ligands and the enhanced reactivity that they impart to Au(I)‐centers after coordination have been found to be the key features that allow an optimization of the reaction conditions until the desired benzo[5]helicenes are obtained with high yield and enantioselectivity. John Wiley and Sons Inc. 2020-10-22 2020-12-21 /pmc/articles/PMC7756570/ /pubmed/32896999 http://dx.doi.org/10.1002/anie.202010021 Text en © 2020 The Authors. Published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Redero, Pablo
Hartung, Thierry
Zhang, Jianwei
Nicholls, Leo D. M.
Zichen, Guo
Simon, Martin
Golz, Christopher
Alcarazo, Manuel
Enantioselective Synthesis of 1‐Aryl Benzo[5]helicenes Using BINOL‐Derived Cationic Phosphonites as Ancillary Ligands
title Enantioselective Synthesis of 1‐Aryl Benzo[5]helicenes Using BINOL‐Derived Cationic Phosphonites as Ancillary Ligands
title_full Enantioselective Synthesis of 1‐Aryl Benzo[5]helicenes Using BINOL‐Derived Cationic Phosphonites as Ancillary Ligands
title_fullStr Enantioselective Synthesis of 1‐Aryl Benzo[5]helicenes Using BINOL‐Derived Cationic Phosphonites as Ancillary Ligands
title_full_unstemmed Enantioselective Synthesis of 1‐Aryl Benzo[5]helicenes Using BINOL‐Derived Cationic Phosphonites as Ancillary Ligands
title_short Enantioselective Synthesis of 1‐Aryl Benzo[5]helicenes Using BINOL‐Derived Cationic Phosphonites as Ancillary Ligands
title_sort enantioselective synthesis of 1‐aryl benzo[5]helicenes using binol‐derived cationic phosphonites as ancillary ligands
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7756570/
https://www.ncbi.nlm.nih.gov/pubmed/32896999
http://dx.doi.org/10.1002/anie.202010021
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