Practical and Scalable Kinetic Resolution of BINOLs Mediated by a Chiral Counterion

BINOLs are valuable and widely used building blocks, chiral ligands, and catalysts that are effective across a remarkable range of different chemical transformations. Here we demonstrate that an ammonium salt catalyzed kinetic resolution of racemic BINOLs with benzyl tosylate proceeds with s up to 4...

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Detalles Bibliográficos
Autores principales: Jones, Benjamin A., Balan, Tudor, Jolliffe, John D., Campbell, Craig D., Smith, Martin D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6492193/
https://www.ncbi.nlm.nih.gov/pubmed/30779415
http://dx.doi.org/10.1002/anie.201814381
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author Jones, Benjamin A.
Balan, Tudor
Jolliffe, John D.
Campbell, Craig D.
Smith, Martin D.
author_facet Jones, Benjamin A.
Balan, Tudor
Jolliffe, John D.
Campbell, Craig D.
Smith, Martin D.
author_sort Jones, Benjamin A.
collection PubMed
description BINOLs are valuable and widely used building blocks, chiral ligands, and catalysts that are effective across a remarkable range of different chemical transformations. Here we demonstrate that an ammonium salt catalyzed kinetic resolution of racemic BINOLs with benzyl tosylate proceeds with s up to 46. This is a scalable and practical process that can be applied across >30 different C (2)‐ and non‐C (2)‐symmetric BINOLs. Implementation of this method enables the enantioselective synthesis of a wide range of BINOL derivatives with over 99:1 e.r.
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spelling pubmed-64921932019-05-07 Practical and Scalable Kinetic Resolution of BINOLs Mediated by a Chiral Counterion Jones, Benjamin A. Balan, Tudor Jolliffe, John D. Campbell, Craig D. Smith, Martin D. Angew Chem Int Ed Engl Communications BINOLs are valuable and widely used building blocks, chiral ligands, and catalysts that are effective across a remarkable range of different chemical transformations. Here we demonstrate that an ammonium salt catalyzed kinetic resolution of racemic BINOLs with benzyl tosylate proceeds with s up to 46. This is a scalable and practical process that can be applied across >30 different C (2)‐ and non‐C (2)‐symmetric BINOLs. Implementation of this method enables the enantioselective synthesis of a wide range of BINOL derivatives with over 99:1 e.r. John Wiley and Sons Inc. 2019-03-05 2019-03-26 /pmc/articles/PMC6492193/ /pubmed/30779415 http://dx.doi.org/10.1002/anie.201814381 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Jones, Benjamin A.
Balan, Tudor
Jolliffe, John D.
Campbell, Craig D.
Smith, Martin D.
Practical and Scalable Kinetic Resolution of BINOLs Mediated by a Chiral Counterion
title Practical and Scalable Kinetic Resolution of BINOLs Mediated by a Chiral Counterion
title_full Practical and Scalable Kinetic Resolution of BINOLs Mediated by a Chiral Counterion
title_fullStr Practical and Scalable Kinetic Resolution of BINOLs Mediated by a Chiral Counterion
title_full_unstemmed Practical and Scalable Kinetic Resolution of BINOLs Mediated by a Chiral Counterion
title_short Practical and Scalable Kinetic Resolution of BINOLs Mediated by a Chiral Counterion
title_sort practical and scalable kinetic resolution of binols mediated by a chiral counterion
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6492193/
https://www.ncbi.nlm.nih.gov/pubmed/30779415
http://dx.doi.org/10.1002/anie.201814381
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