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Enantioselective access to chiral aliphatic amines and alcohols via Ni-catalyzed hydroalkylations

Chiral aliphatic amine and alcohol derivatives are ubiquitous in pharmaceuticals, pesticides, natural products and fine chemicals, yet difficult to access due to the challenge to differentiate between the spatially and electronically similar alkyl groups. Herein, we report a nickel-catalyzed enantio...

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Autores principales: Wang, Shan, Zhang, Jian-Xin, Zhang, Tian-Yi, Meng, Huan, Chen, Bi-Hong, Shu, Wei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8119980/
https://www.ncbi.nlm.nih.gov/pubmed/33986269
http://dx.doi.org/10.1038/s41467-021-22983-7
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author Wang, Shan
Zhang, Jian-Xin
Zhang, Tian-Yi
Meng, Huan
Chen, Bi-Hong
Shu, Wei
author_facet Wang, Shan
Zhang, Jian-Xin
Zhang, Tian-Yi
Meng, Huan
Chen, Bi-Hong
Shu, Wei
author_sort Wang, Shan
collection PubMed
description Chiral aliphatic amine and alcohol derivatives are ubiquitous in pharmaceuticals, pesticides, natural products and fine chemicals, yet difficult to access due to the challenge to differentiate between the spatially and electronically similar alkyl groups. Herein, we report a nickel-catalyzed enantioselective hydroalkylation of acyl enamines and enol esters with alkyl halides to afford enantioenriched α-branched aliphatic acyl amines and esters in good yields with excellent levels of enantioselectivity. The operationally simple protocol provides a straightforward access to chiral secondary alkyl-substituted amine and secondary alkyl-substituted alcohol derivatives from simple starting materials with great functional group tolerance.
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spelling pubmed-81199802021-05-18 Enantioselective access to chiral aliphatic amines and alcohols via Ni-catalyzed hydroalkylations Wang, Shan Zhang, Jian-Xin Zhang, Tian-Yi Meng, Huan Chen, Bi-Hong Shu, Wei Nat Commun Article Chiral aliphatic amine and alcohol derivatives are ubiquitous in pharmaceuticals, pesticides, natural products and fine chemicals, yet difficult to access due to the challenge to differentiate between the spatially and electronically similar alkyl groups. Herein, we report a nickel-catalyzed enantioselective hydroalkylation of acyl enamines and enol esters with alkyl halides to afford enantioenriched α-branched aliphatic acyl amines and esters in good yields with excellent levels of enantioselectivity. The operationally simple protocol provides a straightforward access to chiral secondary alkyl-substituted amine and secondary alkyl-substituted alcohol derivatives from simple starting materials with great functional group tolerance. Nature Publishing Group UK 2021-05-13 /pmc/articles/PMC8119980/ /pubmed/33986269 http://dx.doi.org/10.1038/s41467-021-22983-7 Text en © The Author(s) 2021 https://creativecommons.org/licenses/by/4.0/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/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Wang, Shan
Zhang, Jian-Xin
Zhang, Tian-Yi
Meng, Huan
Chen, Bi-Hong
Shu, Wei
Enantioselective access to chiral aliphatic amines and alcohols via Ni-catalyzed hydroalkylations
title Enantioselective access to chiral aliphatic amines and alcohols via Ni-catalyzed hydroalkylations
title_full Enantioselective access to chiral aliphatic amines and alcohols via Ni-catalyzed hydroalkylations
title_fullStr Enantioselective access to chiral aliphatic amines and alcohols via Ni-catalyzed hydroalkylations
title_full_unstemmed Enantioselective access to chiral aliphatic amines and alcohols via Ni-catalyzed hydroalkylations
title_short Enantioselective access to chiral aliphatic amines and alcohols via Ni-catalyzed hydroalkylations
title_sort enantioselective access to chiral aliphatic amines and alcohols via ni-catalyzed hydroalkylations
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8119980/
https://www.ncbi.nlm.nih.gov/pubmed/33986269
http://dx.doi.org/10.1038/s41467-021-22983-7
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