Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols

We report a protocol for the highly efficient iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones via dynamic kinetic resolution. Using Ir-SpiroPAP (R)-1d as a catalyst, a wide range of chiral diols were prepared in a high yield (80–95%) with a high enantioselectivity (up to...

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Detalles Bibliográficos
Autores principales: Yang, Xiao-Hui, Yue, Hai-Tao, Yu, Na, Li, Yi-Pan, Xie, Jian-Hua, Zhou, Qi-Lin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5396509/
https://www.ncbi.nlm.nih.gov/pubmed/28451302
http://dx.doi.org/10.1039/c6sc04609f
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author Yang, Xiao-Hui
Yue, Hai-Tao
Yu, Na
Li, Yi-Pan
Xie, Jian-Hua
Zhou, Qi-Lin
author_facet Yang, Xiao-Hui
Yue, Hai-Tao
Yu, Na
Li, Yi-Pan
Xie, Jian-Hua
Zhou, Qi-Lin
author_sort Yang, Xiao-Hui
collection PubMed
description We report a protocol for the highly efficient iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones via dynamic kinetic resolution. Using Ir-SpiroPAP (R)-1d as a catalyst, a wide range of chiral diols were prepared in a high yield (80–95%) with a high enantioselectivity (up to 95% ee) under mild reaction conditions. This protocol was used for enantioselective syntheses of (–)-preclamol and a chiral 2,5-disubstituted tetrahydropyran.
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spelling pubmed-53965092017-04-27 Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols Yang, Xiao-Hui Yue, Hai-Tao Yu, Na Li, Yi-Pan Xie, Jian-Hua Zhou, Qi-Lin Chem Sci Chemistry We report a protocol for the highly efficient iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones via dynamic kinetic resolution. Using Ir-SpiroPAP (R)-1d as a catalyst, a wide range of chiral diols were prepared in a high yield (80–95%) with a high enantioselectivity (up to 95% ee) under mild reaction conditions. This protocol was used for enantioselective syntheses of (–)-preclamol and a chiral 2,5-disubstituted tetrahydropyran. Royal Society of Chemistry 2017-03-01 2016-11-15 /pmc/articles/PMC5396509/ /pubmed/28451302 http://dx.doi.org/10.1039/c6sc04609f Text en This journal is © The Royal Society of Chemistry 2016 https://creativecommons.org/licenses/by/3.0/This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/ (https://creativecommons.org/licenses/by/3.0/) ) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Yang, Xiao-Hui
Yue, Hai-Tao
Yu, Na
Li, Yi-Pan
Xie, Jian-Hua
Zhou, Qi-Lin
Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols
title Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols
title_full Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols
title_fullStr Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols
title_full_unstemmed Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols
title_short Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols
title_sort iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5396509/
https://www.ncbi.nlm.nih.gov/pubmed/28451302
http://dx.doi.org/10.1039/c6sc04609f
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