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Highly Enantioselective One-Pot Synthesis of Chiral β-Heterosubstituted Alcohols via Ruthenium–Prolinamide-Catalyzed Asymmetric Transfer Hydrogenation
[Image: see text] The utility of a chiral Ru–prolinamide catalytic system has been demonstrated in one-pot synthesis of optically active β-triazolylethanol and β-hydroxy sulfone derivatives. The said methodology proceeds through asymmetric transfer hydrogenation of in situ formed ketones of the corr...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2018
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644779/ https://www.ncbi.nlm.nih.gov/pubmed/31458000 http://dx.doi.org/10.1021/acsomega.8b01316 |
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author | Vyas, Vijyesh K. Srivastava, Prasenjit Bhatt, Prachi Shende, Vaishali Ghosh, Pushpito Bhanage, Bhalchandra M. |
author_facet | Vyas, Vijyesh K. Srivastava, Prasenjit Bhatt, Prachi Shende, Vaishali Ghosh, Pushpito Bhanage, Bhalchandra M. |
author_sort | Vyas, Vijyesh K. |
collection | PubMed |
description | [Image: see text] The utility of a chiral Ru–prolinamide catalytic system has been demonstrated in one-pot synthesis of optically active β-triazolylethanol and β-hydroxy sulfone derivatives. The said methodology proceeds through asymmetric transfer hydrogenation of in situ formed ketones of the corresponding chiral products. Various chiral prolinamide ligands were screened, and ligand L6 with isopropyl groups substituted at the ortho position has shown excellent activity at 60 °C in aqueous medium producing up to 95% yield and 99.9% enantioselectivity. |
format | Online Article Text |
id | pubmed-6644779 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-66447792019-08-27 Highly Enantioselective One-Pot Synthesis of Chiral β-Heterosubstituted Alcohols via Ruthenium–Prolinamide-Catalyzed Asymmetric Transfer Hydrogenation Vyas, Vijyesh K. Srivastava, Prasenjit Bhatt, Prachi Shende, Vaishali Ghosh, Pushpito Bhanage, Bhalchandra M. ACS Omega [Image: see text] The utility of a chiral Ru–prolinamide catalytic system has been demonstrated in one-pot synthesis of optically active β-triazolylethanol and β-hydroxy sulfone derivatives. The said methodology proceeds through asymmetric transfer hydrogenation of in situ formed ketones of the corresponding chiral products. Various chiral prolinamide ligands were screened, and ligand L6 with isopropyl groups substituted at the ortho position has shown excellent activity at 60 °C in aqueous medium producing up to 95% yield and 99.9% enantioselectivity. American Chemical Society 2018-10-05 /pmc/articles/PMC6644779/ /pubmed/31458000 http://dx.doi.org/10.1021/acsomega.8b01316 Text en Copyright © 2018 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | Vyas, Vijyesh K. Srivastava, Prasenjit Bhatt, Prachi Shende, Vaishali Ghosh, Pushpito Bhanage, Bhalchandra M. Highly Enantioselective One-Pot Synthesis of Chiral β-Heterosubstituted Alcohols via Ruthenium–Prolinamide-Catalyzed Asymmetric Transfer Hydrogenation |
title | Highly Enantioselective One-Pot Synthesis of Chiral
β-Heterosubstituted Alcohols via Ruthenium–Prolinamide-Catalyzed
Asymmetric Transfer Hydrogenation |
title_full | Highly Enantioselective One-Pot Synthesis of Chiral
β-Heterosubstituted Alcohols via Ruthenium–Prolinamide-Catalyzed
Asymmetric Transfer Hydrogenation |
title_fullStr | Highly Enantioselective One-Pot Synthesis of Chiral
β-Heterosubstituted Alcohols via Ruthenium–Prolinamide-Catalyzed
Asymmetric Transfer Hydrogenation |
title_full_unstemmed | Highly Enantioselective One-Pot Synthesis of Chiral
β-Heterosubstituted Alcohols via Ruthenium–Prolinamide-Catalyzed
Asymmetric Transfer Hydrogenation |
title_short | Highly Enantioselective One-Pot Synthesis of Chiral
β-Heterosubstituted Alcohols via Ruthenium–Prolinamide-Catalyzed
Asymmetric Transfer Hydrogenation |
title_sort | highly enantioselective one-pot synthesis of chiral
β-heterosubstituted alcohols via ruthenium–prolinamide-catalyzed
asymmetric transfer hydrogenation |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644779/ https://www.ncbi.nlm.nih.gov/pubmed/31458000 http://dx.doi.org/10.1021/acsomega.8b01316 |
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