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铱催化二酮的还原胺化和转移氢化反应：通往β-和γ-氨基醇的途径。

Ir-catalyzed reductive amination and transfer hydrogenation of diketones: access to β- and γ-amino alcohols.

作者信息

Tong Jinghui, Guo Shilin, Zhu Huajie, Ouyang Lu, Liao Jianhua, Li Youchun

机构信息

School of Pharmacy, Gannan Medical University Ganzhou 341000 Jiangxi Province P. R. China

The Affiliated Ganzhou Hospital, Jiangxi Medical College, Nanchang University Ganzhou 341000 Jiangxi Province P. R. China.

出版信息

RSC Adv. 2024 Nov 29;14(51):38105-38109. doi: 10.1039/d4ra07386j. eCollection 2024 Nov 25.

DOI:10.1039/d4ra07386j
PMID:39619808
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11606304/
Abstract

β- and γ-Amino alcohols are among the most significant structural motifs in pharmacologically active molecules and pharmaceuticals. Herein, a protocol for the construction of β- and γ-amino alcohols reductive amination and transfer hydrogenation of diketones with aromatic amines is described. This reaction is performed by utilizing iridium complexes as catalysts and HCOH as a hydrogen donor to deliver a library of β- and γ-amino alcohols under mild and operationally simple conditions. Successful scale-up performance was also conducted under standard conditions.

摘要

β-和γ-氨基醇是药理活性分子和药物中最重要的结构基序之一。本文描述了一种通过二酮与芳香胺的还原胺化和转移氢化反应构建β-和γ-氨基醇的方法。该反应以铱配合物为催化剂，以HCOH为氢供体，在温和且操作简单的条件下生成一系列β-和γ-氨基醇。在标准条件下还成功进行了放大反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fe5a/11606304/52775772c2c3/d4ra07386j-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fe5a/11606304/5abec01b9527/d4ra07386j-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fe5a/11606304/3d27e3daec1a/d4ra07386j-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fe5a/11606304/e9b6112abe18/d4ra07386j-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fe5a/11606304/52775772c2c3/d4ra07386j-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fe5a/11606304/5abec01b9527/d4ra07386j-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fe5a/11606304/3d27e3daec1a/d4ra07386j-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fe5a/11606304/e9b6112abe18/d4ra07386j-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fe5a/11606304/52775772c2c3/d4ra07386j-s4.jpg

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本文引用的文献

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Construction of -Aryl-Substituted Pyrrolidines by Successive Reductive Amination of Diketones via Transfer Hydrogenation.通过转移氢化法对二酮进行连续还原胺化反应构建 -芳基取代的吡咯烷
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2
Asymmetric Reductive Amination of α-Keto Acids Using Ir-Based Hydrogen Transfer Catalysts: An Access to Unprotected Unnatural α-Amino Acids.使用铱基氢转移催化剂对α-酮酸进行不对称还原胺化反应：一种合成未保护的非天然α-氨基酸的方法。
Org Lett. 2024 Feb 23;26(7):1426-1431. doi: 10.1021/acs.orglett.3c04378. Epub 2024 Feb 9.
3
Recent advances of Cp*Ir complexes for transfer hydrogenation: focus on formic acid/formate as hydrogen donors.
用于转移氢化的Cp*Ir配合物的最新进展：聚焦于甲酸/甲酸盐作为氢供体
Org Biomol Chem. 2023 Sep 27;21(37):7484-7497. doi: 10.1039/d3ob01034a.
4
Synthesis of -alkoxy amines and hydroxylamines the iridium-catalyzed transfer hydrogenation of oximes.-烷氧基胺和羟胺的合成：肟的铱催化转移氢化。
Org Biomol Chem. 2022 Aug 17;20(32):6394-6399. doi: 10.1039/d2ob01084d.
5
Manganese-Catalyzed Asymmetric Formal Hydroamination of Allylic Alcohols: A Remarkable Macrocyclic Ligand Effect.锰催化的烯丙醇不对称形式氢胺化反应：显著的大环配体效应
Angew Chem Int Ed Engl. 2022 Jun 27;61(26):e202202972. doi: 10.1002/anie.202202972. Epub 2022 May 3.
6
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