Integrated Cobaloxime and Mesoporous Silica-Supported Ruthenium/Diamine Co-Catalysis for One-Pot Hydration/Reduction Enantioselective Sequential Reaction of Alkynes

This study developed a cost-efficient hydration/asymmetric transfer hydrogenation (ATH) process for the one-pot synthesis of valuable chiral alcohols from alkynes. During this process, the initial homogeneous cobaloxime-catalyzed hydration of alkynes was followed by heterogeneous Ru/diamine-catalyze...

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Autores principales: Liu, Zeyang, Wang, Yongjie, Liu, Kaihong, Wang, Shanshan, Liao, Haocheng, Zhu, Yuanli, Hou, Baoming, Tan, Chunxia, Liu, Guohua
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8493125/
https://www.ncbi.nlm.nih.gov/pubmed/34631659
http://dx.doi.org/10.3389/fchem.2021.732542
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author Liu, Zeyang
Wang, Yongjie
Liu, Kaihong
Wang, Shanshan
Liao, Haocheng
Zhu, Yuanli
Hou, Baoming
Tan, Chunxia
Liu, Guohua
author_facet Liu, Zeyang
Wang, Yongjie
Liu, Kaihong
Wang, Shanshan
Liao, Haocheng
Zhu, Yuanli
Hou, Baoming
Tan, Chunxia
Liu, Guohua
author_sort Liu, Zeyang
collection PubMed
description This study developed a cost-efficient hydration/asymmetric transfer hydrogenation (ATH) process for the one-pot synthesis of valuable chiral alcohols from alkynes. During this process, the initial homogeneous cobaloxime-catalyzed hydration of alkynes was followed by heterogeneous Ru/diamine-catalyzed ATH transformation of the in-situ generated ketones, which provided varieties of chiral alcohols in good yields with up to 99% ee values. The immobilized Ru/diamine catalyst could be recycled at least three times before its deactivation in the sequential reaction system. This work shows a general method for developing one-pot asymmetric sequential catalysis towards sustainable organic synthesis.
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spelling pubmed-84931252021-10-07 Integrated Cobaloxime and Mesoporous Silica-Supported Ruthenium/Diamine Co-Catalysis for One-Pot Hydration/Reduction Enantioselective Sequential Reaction of Alkynes Liu, Zeyang Wang, Yongjie Liu, Kaihong Wang, Shanshan Liao, Haocheng Zhu, Yuanli Hou, Baoming Tan, Chunxia Liu, Guohua Front Chem Chemistry This study developed a cost-efficient hydration/asymmetric transfer hydrogenation (ATH) process for the one-pot synthesis of valuable chiral alcohols from alkynes. During this process, the initial homogeneous cobaloxime-catalyzed hydration of alkynes was followed by heterogeneous Ru/diamine-catalyzed ATH transformation of the in-situ generated ketones, which provided varieties of chiral alcohols in good yields with up to 99% ee values. The immobilized Ru/diamine catalyst could be recycled at least three times before its deactivation in the sequential reaction system. This work shows a general method for developing one-pot asymmetric sequential catalysis towards sustainable organic synthesis. Frontiers Media S.A. 2021-09-22 /pmc/articles/PMC8493125/ /pubmed/34631659 http://dx.doi.org/10.3389/fchem.2021.732542 Text en Copyright © 2021 Liu, Wang, Liu, Wang, Liao, Zhu, Hou, Tan and Liu. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Liu, Zeyang
Wang, Yongjie
Liu, Kaihong
Wang, Shanshan
Liao, Haocheng
Zhu, Yuanli
Hou, Baoming
Tan, Chunxia
Liu, Guohua
Integrated Cobaloxime and Mesoporous Silica-Supported Ruthenium/Diamine Co-Catalysis for One-Pot Hydration/Reduction Enantioselective Sequential Reaction of Alkynes
title Integrated Cobaloxime and Mesoporous Silica-Supported Ruthenium/Diamine Co-Catalysis for One-Pot Hydration/Reduction Enantioselective Sequential Reaction of Alkynes
title_full Integrated Cobaloxime and Mesoporous Silica-Supported Ruthenium/Diamine Co-Catalysis for One-Pot Hydration/Reduction Enantioselective Sequential Reaction of Alkynes
title_fullStr Integrated Cobaloxime and Mesoporous Silica-Supported Ruthenium/Diamine Co-Catalysis for One-Pot Hydration/Reduction Enantioselective Sequential Reaction of Alkynes
title_full_unstemmed Integrated Cobaloxime and Mesoporous Silica-Supported Ruthenium/Diamine Co-Catalysis for One-Pot Hydration/Reduction Enantioselective Sequential Reaction of Alkynes
title_short Integrated Cobaloxime and Mesoporous Silica-Supported Ruthenium/Diamine Co-Catalysis for One-Pot Hydration/Reduction Enantioselective Sequential Reaction of Alkynes
title_sort integrated cobaloxime and mesoporous silica-supported ruthenium/diamine co-catalysis for one-pot hydration/reduction enantioselective sequential reaction of alkynes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8493125/
https://www.ncbi.nlm.nih.gov/pubmed/34631659
http://dx.doi.org/10.3389/fchem.2021.732542
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