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The combination of asymmetric hydrogenation of olefins and direct reductive amination

Asymmetric hydrogenation (AH) and direct reductive amination (DRA) are both efficient transformations frequently utilized in industry. Here we combine the asymmetric hydrogenation of prochiral olefins and direct reductive amination of aldehydes in one step using hydrogen gas as the common reductant...

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Autores principales: Yuan, Shuai, Gao, Guorui, Wang, Lili, Liu, Cungang, Wan, Lei, Huang, Haizhou, Geng, Huiling, Chang, Mingxin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6992772/
https://www.ncbi.nlm.nih.gov/pubmed/32001706
http://dx.doi.org/10.1038/s41467-020-14475-x
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author Yuan, Shuai
Gao, Guorui
Wang, Lili
Liu, Cungang
Wan, Lei
Huang, Haizhou
Geng, Huiling
Chang, Mingxin
author_facet Yuan, Shuai
Gao, Guorui
Wang, Lili
Liu, Cungang
Wan, Lei
Huang, Haizhou
Geng, Huiling
Chang, Mingxin
author_sort Yuan, Shuai
collection PubMed
description Asymmetric hydrogenation (AH) and direct reductive amination (DRA) are both efficient transformations frequently utilized in industry. Here we combine the asymmetric hydrogenation of prochiral olefins and direct reductive amination of aldehydes in one step using hydrogen gas as the common reductant and a rhodium-Segphos complex as the catalyst. With this strategy, the efficiency for the synthesis of the corresponding chiral amino compounds is significantly improved. The practical application of this synthetic approach is demonstrated by the facile synthesis of chiral 3-phenyltetrahydroquinoline and 3-benzylindoline compounds.
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spelling pubmed-69927722020-02-03 The combination of asymmetric hydrogenation of olefins and direct reductive amination Yuan, Shuai Gao, Guorui Wang, Lili Liu, Cungang Wan, Lei Huang, Haizhou Geng, Huiling Chang, Mingxin Nat Commun Article Asymmetric hydrogenation (AH) and direct reductive amination (DRA) are both efficient transformations frequently utilized in industry. Here we combine the asymmetric hydrogenation of prochiral olefins and direct reductive amination of aldehydes in one step using hydrogen gas as the common reductant and a rhodium-Segphos complex as the catalyst. With this strategy, the efficiency for the synthesis of the corresponding chiral amino compounds is significantly improved. The practical application of this synthetic approach is demonstrated by the facile synthesis of chiral 3-phenyltetrahydroquinoline and 3-benzylindoline compounds. Nature Publishing Group UK 2020-01-30 /pmc/articles/PMC6992772/ /pubmed/32001706 http://dx.doi.org/10.1038/s41467-020-14475-x Text en © The Author(s) 2020 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
Yuan, Shuai
Gao, Guorui
Wang, Lili
Liu, Cungang
Wan, Lei
Huang, Haizhou
Geng, Huiling
Chang, Mingxin
The combination of asymmetric hydrogenation of olefins and direct reductive amination
title The combination of asymmetric hydrogenation of olefins and direct reductive amination
title_full The combination of asymmetric hydrogenation of olefins and direct reductive amination
title_fullStr The combination of asymmetric hydrogenation of olefins and direct reductive amination
title_full_unstemmed The combination of asymmetric hydrogenation of olefins and direct reductive amination
title_short The combination of asymmetric hydrogenation of olefins and direct reductive amination
title_sort combination of asymmetric hydrogenation of olefins and direct reductive amination
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6992772/
https://www.ncbi.nlm.nih.gov/pubmed/32001706
http://dx.doi.org/10.1038/s41467-020-14475-x
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