Gold(I)‐Catalyzed Cycloisomerization of 3‐Alkoxyl‐1,6‐diynes: A Facile Access to Bicyclo[2.2.1]hept‐5‐en‐2‐ones

A novel gold‐catalyzed cycloisomerization of 1,6‐diynes was achieved, providing an atom‐economic approach to a diverse set of bicyclo[2.2.1]hept‐5‐en‐2‐ones in moderate to good yields. With unsymmetrical starting materials with two different internal alkynyl substituents, to some extent, the regiose...

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Autores principales: Hu, Chao, Wang, Tao, Rudolph, Matthias, Oeser, Thomas, Asiri, Abdullah M., Hashmi, A. Stephen K.
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/PMC7318145/
https://www.ncbi.nlm.nih.gov/pubmed/31972059
http://dx.doi.org/10.1002/anie.201914284
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author Hu, Chao
Wang, Tao
Rudolph, Matthias
Oeser, Thomas
Asiri, Abdullah M.
Hashmi, A. Stephen K.
author_facet Hu, Chao
Wang, Tao
Rudolph, Matthias
Oeser, Thomas
Asiri, Abdullah M.
Hashmi, A. Stephen K.
author_sort Hu, Chao
collection PubMed
description A novel gold‐catalyzed cycloisomerization of 1,6‐diynes was achieved, providing an atom‐economic approach to a diverse set of bicyclo[2.2.1]hept‐5‐en‐2‐ones in moderate to good yields. With unsymmetrical starting materials with two different internal alkynyl substituents, to some extent, the regioselectivity could be controlled by both electronic and steric factors. This unprecedented reactivity pattern may inspire new and unconventional strategies for the preparation of bridged ring systems.
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spelling pubmed-73181452020-06-29 Gold(I)‐Catalyzed Cycloisomerization of 3‐Alkoxyl‐1,6‐diynes: A Facile Access to Bicyclo[2.2.1]hept‐5‐en‐2‐ones Hu, Chao Wang, Tao Rudolph, Matthias Oeser, Thomas Asiri, Abdullah M. Hashmi, A. Stephen K. Angew Chem Int Ed Engl Communications A novel gold‐catalyzed cycloisomerization of 1,6‐diynes was achieved, providing an atom‐economic approach to a diverse set of bicyclo[2.2.1]hept‐5‐en‐2‐ones in moderate to good yields. With unsymmetrical starting materials with two different internal alkynyl substituents, to some extent, the regioselectivity could be controlled by both electronic and steric factors. This unprecedented reactivity pattern may inspire new and unconventional strategies for the preparation of bridged ring systems. John Wiley and Sons Inc. 2020-03-24 2020-05-25 /pmc/articles/PMC7318145/ /pubmed/31972059 http://dx.doi.org/10.1002/anie.201914284 Text en © 2020 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-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
Hu, Chao
Wang, Tao
Rudolph, Matthias
Oeser, Thomas
Asiri, Abdullah M.
Hashmi, A. Stephen K.
Gold(I)‐Catalyzed Cycloisomerization of 3‐Alkoxyl‐1,6‐diynes: A Facile Access to Bicyclo[2.2.1]hept‐5‐en‐2‐ones
title Gold(I)‐Catalyzed Cycloisomerization of 3‐Alkoxyl‐1,6‐diynes: A Facile Access to Bicyclo[2.2.1]hept‐5‐en‐2‐ones
title_full Gold(I)‐Catalyzed Cycloisomerization of 3‐Alkoxyl‐1,6‐diynes: A Facile Access to Bicyclo[2.2.1]hept‐5‐en‐2‐ones
title_fullStr Gold(I)‐Catalyzed Cycloisomerization of 3‐Alkoxyl‐1,6‐diynes: A Facile Access to Bicyclo[2.2.1]hept‐5‐en‐2‐ones
title_full_unstemmed Gold(I)‐Catalyzed Cycloisomerization of 3‐Alkoxyl‐1,6‐diynes: A Facile Access to Bicyclo[2.2.1]hept‐5‐en‐2‐ones
title_short Gold(I)‐Catalyzed Cycloisomerization of 3‐Alkoxyl‐1,6‐diynes: A Facile Access to Bicyclo[2.2.1]hept‐5‐en‐2‐ones
title_sort gold(i)‐catalyzed cycloisomerization of 3‐alkoxyl‐1,6‐diynes: a facile access to bicyclo[2.2.1]hept‐5‐en‐2‐ones
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7318145/
https://www.ncbi.nlm.nih.gov/pubmed/31972059
http://dx.doi.org/10.1002/anie.201914284
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