Pd(OAc)(2)-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines

Asymmetric hydrogenation of sterically hindered substrates still constitutes a long-standing challenge in the area of asymmetric catalysis. Herein, an efficient palladium acetate (an inexpensive Pd salt with low toxicity) catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines is rea...

Descripción completa

Detalles Bibliográficos
Autores principales: Chen, Jianzhong, Zhang, Zhenfeng, Li, Bowen, Li, Feilong, Wang, Yulin, Zhao, Min, Gridnev, Ilya D., Imamoto, Tsuneo, Zhang, Wanbin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2018
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6258694/
https://www.ncbi.nlm.nih.gov/pubmed/30479338
http://dx.doi.org/10.1038/s41467-018-07462-w
_version_ 1783374536615395328
author Chen, Jianzhong
Zhang, Zhenfeng
Li, Bowen
Li, Feilong
Wang, Yulin
Zhao, Min
Gridnev, Ilya D.
Imamoto, Tsuneo
Zhang, Wanbin
author_facet Chen, Jianzhong
Zhang, Zhenfeng
Li, Bowen
Li, Feilong
Wang, Yulin
Zhao, Min
Gridnev, Ilya D.
Imamoto, Tsuneo
Zhang, Wanbin
author_sort Chen, Jianzhong
collection PubMed
description Asymmetric hydrogenation of sterically hindered substrates still constitutes a long-standing challenge in the area of asymmetric catalysis. Herein, an efficient palladium acetate (an inexpensive Pd salt with low toxicity) catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines is realized with high catalytic activities (S/C up to 5000) and excellent enantioselectivities (ee up to 99.9%). Quantum chemical calculations suggest that uniformly high enantioselectivities are observed due to the structurally different S- and R-reaction pathways.
format Online
Article
Text
id pubmed-6258694
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher Nature Publishing Group UK
record_format MEDLINE/PubMed
spelling pubmed-62586942018-11-29 Pd(OAc)(2)-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines Chen, Jianzhong Zhang, Zhenfeng Li, Bowen Li, Feilong Wang, Yulin Zhao, Min Gridnev, Ilya D. Imamoto, Tsuneo Zhang, Wanbin Nat Commun Article Asymmetric hydrogenation of sterically hindered substrates still constitutes a long-standing challenge in the area of asymmetric catalysis. Herein, an efficient palladium acetate (an inexpensive Pd salt with low toxicity) catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines is realized with high catalytic activities (S/C up to 5000) and excellent enantioselectivities (ee up to 99.9%). Quantum chemical calculations suggest that uniformly high enantioselectivities are observed due to the structurally different S- and R-reaction pathways. Nature Publishing Group UK 2018-11-27 /pmc/articles/PMC6258694/ /pubmed/30479338 http://dx.doi.org/10.1038/s41467-018-07462-w Text en © The Author(s) 2018 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Chen, Jianzhong
Zhang, Zhenfeng
Li, Bowen
Li, Feilong
Wang, Yulin
Zhao, Min
Gridnev, Ilya D.
Imamoto, Tsuneo
Zhang, Wanbin
Pd(OAc)(2)-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines
title Pd(OAc)(2)-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines
title_full Pd(OAc)(2)-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines
title_fullStr Pd(OAc)(2)-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines
title_full_unstemmed Pd(OAc)(2)-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines
title_short Pd(OAc)(2)-catalyzed asymmetric hydrogenation of sterically hindered N-tosylimines
title_sort pd(oac)(2)-catalyzed asymmetric hydrogenation of sterically hindered n-tosylimines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6258694/
https://www.ncbi.nlm.nih.gov/pubmed/30479338
http://dx.doi.org/10.1038/s41467-018-07462-w
work_keys_str_mv AT chenjianzhong pdoac2catalyzedasymmetrichydrogenationofstericallyhinderedntosylimines
AT zhangzhenfeng pdoac2catalyzedasymmetrichydrogenationofstericallyhinderedntosylimines
AT libowen pdoac2catalyzedasymmetrichydrogenationofstericallyhinderedntosylimines
AT lifeilong pdoac2catalyzedasymmetrichydrogenationofstericallyhinderedntosylimines
AT wangyulin pdoac2catalyzedasymmetrichydrogenationofstericallyhinderedntosylimines
AT zhaomin pdoac2catalyzedasymmetrichydrogenationofstericallyhinderedntosylimines
AT gridnevilyad pdoac2catalyzedasymmetrichydrogenationofstericallyhinderedntosylimines
AT imamototsuneo pdoac2catalyzedasymmetrichydrogenationofstericallyhinderedntosylimines
AT zhangwanbin pdoac2catalyzedasymmetrichydrogenationofstericallyhinderedntosylimines

Ejemplares similares