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醌催化的氧化脱甲酰基反应：由氨基醇合成亚胺

Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols.

作者信息

Liu Xinyun, Phan Johnny H, Haugeberg Benjamin J, Londhe Shrikant S, Clift Michael D

机构信息

Department of Chemistry, The University of Kansas, 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence, KS, 66045, United States.

出版信息

Beilstein J Org Chem. 2017 Dec 28;13:2895-2901. doi: 10.3762/bjoc.13.282. eCollection 2017.

DOI:10.3762/bjoc.13.282
PMID:29564017
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5753116/
Abstract

A new method for imine synthesis by way of quinone-catalyzed oxidative deformylation of 1,2-amino alcohols is reported. A wide range of readily accessible amino alcohols and primary amines can be reacted to provide N-protected imine products. The methodology presented provides a novel organocatalytic approach for imine synthesis and demonstrates the synthetic versatility of quinone-catalyzed oxidative C-C bond cleavage.

摘要

报道了一种通过醌催化1,2-氨基醇的氧化脱甲酰化反应合成亚胺的新方法。多种易于获得的氨基醇和伯胺可以反应生成N-保护的亚胺产物。所提出的方法为亚胺合成提供了一种新颖的有机催化方法，并展示了醌催化的氧化C-C键裂解的合成多功能性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/47a2/5753116/47627594361a/Beilstein_J_Org_Chem-13-2895-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/47a2/5753116/6755bcfacfe9/Beilstein_J_Org_Chem-13-2895-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/47a2/5753116/23f32eb576d7/Beilstein_J_Org_Chem-13-2895-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/47a2/5753116/ea5439775f38/Beilstein_J_Org_Chem-13-2895-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/47a2/5753116/47627594361a/Beilstein_J_Org_Chem-13-2895-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/47a2/5753116/6755bcfacfe9/Beilstein_J_Org_Chem-13-2895-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/47a2/5753116/23f32eb576d7/Beilstein_J_Org_Chem-13-2895-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/47a2/5753116/ea5439775f38/Beilstein_J_Org_Chem-13-2895-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/47a2/5753116/47627594361a/Beilstein_J_Org_Chem-13-2895-g005.jpg

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本文引用的文献

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Homologation of α-aryl amino acids through quinone-catalyzed decarboxylation/Mukaiyama-Mannich addition.通过醌催化脱羧/ Mukaiyama-曼尼希加成实现α-芳基氨基酸的同源化。
Chem Commun (Camb). 2017 Mar 9;53(21):3062-3065. doi: 10.1039/c7cc00485k.
2
Enantioselective Decarboxylative Arylation of α-Amino Acids via the Merger of Photoredox and Nickel Catalysis.通过光氧化还原与镍催化相结合实现α-氨基酸的对映选择性脱羧芳基化反应
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Amine Functionalization via Oxidative Photoredox Catalysis: Methodology Development and Complex Molecule Synthesis.
通过氧化光氧化还原催化实现胺功能化：方法学发展与复杂分子合成
Acc Chem Res. 2015 May 19;48(5):1474-84. doi: 10.1021/acs.accounts.5b00068. Epub 2015 May 7.
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Common metal of copper(0) as an efficient catalyst for preparation of nitriles and imines by controlling additives.零价铜这种常见金属作为通过控制添加剂制备腈类和亚胺类化合物的高效催化剂。
Chem Commun (Camb). 2014 May 30;50(42):5637-40. doi: 10.1039/c4cc01389a.
5
Decarboxylative arylation of α-amino acids via photoredox catalysis: a one-step conversion of biomass to drug pharmacophore.通过光氧化还原催化实现α-氨基酸的脱羧芳基化：生物质向药物药效基团的一步转化。
J Am Chem Soc. 2014 Apr 9;136(14):5257-60. doi: 10.1021/ja501621q. Epub 2014 Mar 31.
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Highly efficient aerobic oxidation of various amines using Pd3Pb intermetallic compounds as catalysts.使用 Pd3Pb 金属间化合物作为催化剂，实现各种胺类的高效有氧氧化。
Chem Commun (Camb). 2014 Mar 28;50(25):3277-80. doi: 10.1039/c4cc00024b. Epub 2014 Feb 14.
7
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J Am Chem Soc. 2014 Jan 8;136(1):506-12. doi: 10.1021/ja411692v. Epub 2013 Dec 18.
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9
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