Gold‐Catalyzed Atroposelective Synthesis of 1,1′‐Binaphthalene‐2,3′‐diols

A highly atroposelective (up to 97 % ee) Au‐catalyzed synthesis of 1,1′‐binaphthalene‐2,3′‐diols is reported starting from a range of substituted benzyl alkynones. Essential for the achievement of high enantioselectivity during the key assembly of the naphto‐3‐ol unit is the use of TADDOL‐derived α‐...

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Autores principales: Zhang, Jianwei, 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/PMC7155015/
https://www.ncbi.nlm.nih.gov/pubmed/31859408
http://dx.doi.org/10.1002/anie.201915456
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author Zhang, Jianwei
Simon, Martin
Golz, Christopher
Alcarazo, Manuel
author_facet Zhang, Jianwei
Simon, Martin
Golz, Christopher
Alcarazo, Manuel
author_sort Zhang, Jianwei
collection PubMed
description A highly atroposelective (up to 97 % ee) Au‐catalyzed synthesis of 1,1′‐binaphthalene‐2,3′‐diols is reported starting from a range of substituted benzyl alkynones. Essential for the achievement of high enantioselectivity during the key assembly of the naphto‐3‐ol unit is the use of TADDOL‐derived α‐cationic phosphonites as ancillary ligands. Preliminary results demonstrate that the transformation of the obtained binaphthyls into axially chiral monodentate phosphines is possible without degradation of enantiopurity.
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spelling pubmed-71550152020-04-15 Gold‐Catalyzed Atroposelective Synthesis of 1,1′‐Binaphthalene‐2,3′‐diols Zhang, Jianwei Simon, Martin Golz, Christopher Alcarazo, Manuel Angew Chem Int Ed Engl Communications A highly atroposelective (up to 97 % ee) Au‐catalyzed synthesis of 1,1′‐binaphthalene‐2,3′‐diols is reported starting from a range of substituted benzyl alkynones. Essential for the achievement of high enantioselectivity during the key assembly of the naphto‐3‐ol unit is the use of TADDOL‐derived α‐cationic phosphonites as ancillary ligands. Preliminary results demonstrate that the transformation of the obtained binaphthyls into axially chiral monodentate phosphines is possible without degradation of enantiopurity. John Wiley and Sons Inc. 2020-01-23 2020-03-27 /pmc/articles/PMC7155015/ /pubmed/31859408 http://dx.doi.org/10.1002/anie.201915456 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
Zhang, Jianwei
Simon, Martin
Golz, Christopher
Alcarazo, Manuel
Gold‐Catalyzed Atroposelective Synthesis of 1,1′‐Binaphthalene‐2,3′‐diols
title Gold‐Catalyzed Atroposelective Synthesis of 1,1′‐Binaphthalene‐2,3′‐diols
title_full Gold‐Catalyzed Atroposelective Synthesis of 1,1′‐Binaphthalene‐2,3′‐diols
title_fullStr Gold‐Catalyzed Atroposelective Synthesis of 1,1′‐Binaphthalene‐2,3′‐diols
title_full_unstemmed Gold‐Catalyzed Atroposelective Synthesis of 1,1′‐Binaphthalene‐2,3′‐diols
title_short Gold‐Catalyzed Atroposelective Synthesis of 1,1′‐Binaphthalene‐2,3′‐diols
title_sort gold‐catalyzed atroposelective synthesis of 1,1′‐binaphthalene‐2,3′‐diols
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7155015/
https://www.ncbi.nlm.nih.gov/pubmed/31859408
http://dx.doi.org/10.1002/anie.201915456
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AT golzchristopher goldcatalyzedatroposelectivesynthesisof11binaphthalene23diols
AT alcarazomanuel goldcatalyzedatroposelectivesynthesisof11binaphthalene23diols

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