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镍催化的 N-酰基烯胺的不对称氢芳基化反应合成手性苄胺。

NiH-catalyzed asymmetric hydroarylation of N-acyl enamines to chiral benzylamines.

机构信息

State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China.

出版信息

Nat Commun. 2021 Jan 27;12(1):638. doi: 10.1038/s41467-020-20888-5.

DOI:10.1038/s41467-020-20888-5
PMID:33504793
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7841163/
Abstract

Enantiomerically pure chiral amines and related amide derivatives are privilege motifs in many pharmacologically active molecules. In comparison to the well-established hydroamination, the transition metal-catalysed asymmetric hydrofunctionalization of enamines provides a complementary approach for their construction. Here we report a NiH-catalysed enantio- and regioselective reductive hydroarylation of N-acyl enamines, allowing for the practical access to a broad range of structurally diverse, enantioenriched benzylamines under mild, operationally simple reaction conditions.

摘要

对映体纯手性胺和相关酰胺衍生物是许多药理活性分子中的重要结构单元。与成熟的氨氢化反应相比,烯胺的过渡金属催化不对称氢官能化反应为其构建提供了一种互补的方法。在这里,我们报告了 NiH 催化的 N-酰基烯胺的对映选择性和区域选择性还原氢芳基化反应,在温和、操作简单的反应条件下,可实际获得广泛的结构多样的、对映体富集的苄胺。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3421/7841163/a0db30385044/41467_2020_20888_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3421/7841163/67cfc2e4eb40/41467_2020_20888_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3421/7841163/6c19f7c6d940/41467_2020_20888_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3421/7841163/f6db01c313bb/41467_2020_20888_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3421/7841163/f3a4dc1589bb/41467_2020_20888_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3421/7841163/a0db30385044/41467_2020_20888_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3421/7841163/67cfc2e4eb40/41467_2020_20888_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3421/7841163/6c19f7c6d940/41467_2020_20888_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3421/7841163/f6db01c313bb/41467_2020_20888_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3421/7841163/f3a4dc1589bb/41467_2020_20888_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3421/7841163/a0db30385044/41467_2020_20888_Fig5_HTML.jpg

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Regio- and Enantioselective Ni-Catalyzed Formal Hydroalkylation, Hydrobenzylation, and Hydropropargylation of Acrylamides to α-Tertiary Amides.
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