铜促进烯烃的氧胺化反应立体选择性合成吗啡啉。
Stereoselective synthesis of morpholines via copper-promoted oxyamination of alkenes.
机构信息
Department of Chemistry, The State University of New York at Buffalo, Buffalo, New York 14260, USA.
出版信息
Org Lett. 2012 Sep 7;14(17):4482-5. doi: 10.1021/ol301984b. Epub 2012 Aug 15.
Abstract
A new copper(II) 2-ethylhexanoate-promoted addition of an alcohol and an amine across an alkene (oxyamination) is reported. The alcohol addition is intramolecular, while coupling with the amine occurs intermolecularly. Several 2-aminomethyl morpholines were synthesized in good to excellent yields and diastereoselectivities.
摘要
报道了一种新的铜(II) 2-乙基己酸酯促进的醇和胺与烯烃（肟化）加成反应。醇的加成是分子内的，而与胺的偶联是分子间的。几种 2-氨甲基吗啉以良好到优异的产率和非对映选择性合成。
相似文献
1
Stereoselective synthesis of morpholines via copper-promoted oxyamination of alkenes.铜促进烯烃的氧胺化反应立体选择性合成吗啡啉。
Org Lett. 2012 Sep 7;14(17):4482-5. doi: 10.1021/ol301984b. Epub 2012 Aug 15.
2
Stereoselective and Regioselective Synthesis of Heterocycles via Copper-Catalyzed Additions of Amine Derivatives and Alcohols to Alkenes.通过铜催化的胺衍生物和醇对烯烃的加成反应进行的立体选择性和区域选择性杂环合成。
J Org Chem. 2017 Nov 3;82(21):11311-11325. doi: 10.1021/acs.joc.7b02072. Epub 2017 Sep 29.
3
Sultam synthesis via Cu-catalyzed intermolecular carboamination of alkenes with N-fluorobenzenesulfonimide.通过铜催化的烯烃与 N-氟代苯磺酰胺的分子间碳氨化反应合成磺酰胺。
Org Lett. 2013 May 17;15(10):2502-5. doi: 10.1021/ol4009848. Epub 2013 Apr 29.
4
Stereoselective isoxazolidine synthesis via copper-catalyzed alkene aminooxygenation.铜催化烯烃氮氧环化反应立体选择性合成异噁唑烷。
J Org Chem. 2012 Sep 7;77(17):7755-60. doi: 10.1021/jo3013226. Epub 2012 Aug 15.
5
Diastereo- and enantioselective copper-catalyzed intramolecular carboamination of alkenes for the synthesis of hexahydro-1H-benz[f]indoles.铜催化的非对映选择性和对映选择性的烯烃内碳酰胺化反应在六氢-1H-苯并[f]吲哚合成中的应用。
Org Lett. 2010 Nov 5;12(21):4739-41. doi: 10.1021/ol102233g.
6
Copper-catalyzed enantioselective intramolecular alkene amination/intermolecular Heck-type coupling cascade.铜催化的对映选择性内烯烃胺化/分子间 Heck 型偶联级联反应。
J Am Chem Soc. 2012 Feb 1;134(4):2020-3. doi: 10.1021/ja211272v. Epub 2012 Jan 24.
7
Copper-catalyzed aerobic oxidative intramolecular alkene C-H amination leading to N-heterocycles.铜催化有氧氧化的分子内烯烃 C-H 胺化反应生成 N-杂环化合物。
Org Lett. 2011 Jul 15;13(14):3694-7. doi: 10.1021/ol2013395. Epub 2011 Jun 22.
8
Copper-catalyzed enantioselective formal hydroamination of oxa- and azabicyclic alkenes with hydrosilanes and hydroxylamines.铜催化的手性氧杂和氮杂双环烯烃与硅烷和羟胺的对映选择性形式氢化胺化反应。
Org Lett. 2014 Mar 7;16(5):1498-501. doi: 10.1021/ol5003219. Epub 2014 Feb 20.
9
Stereoselective rhodium-catalyzed amination of alkenes.立体选择性铑催化烯烃的胺化反应。
Org Lett. 2011 Oct 21;13(20):5460-3. doi: 10.1021/ol2021516. Epub 2011 Sep 15.
10
Photocatalytic Oxyamination of Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis.光催化烯烃的氧胺化反应：光氧化还原催化中铜(II)盐作为末端氧化剂。
Org Lett. 2018 Nov 16;20(22):7345-7350. doi: 10.1021/acs.orglett.8b03345. Epub 2018 Nov 8.
引用本文的文献
1
Halonium Catalysis: An Underutilized and Underexplored Catalytic Concept in Olefin Functionalizations.卤鎓催化：烯烃官能团化中一个未充分利用和探索不足的催化概念。
Synlett. 2021 Apr;32(6):539-544. doi: 10.1055/a-1277-8669. Epub 2020 Oct 2.
2
Asymmetric hydrogenation for the synthesis of 2-substituted chiral morpholines.用于合成2-取代手性吗啉的不对称氢化反应。
Chem Sci. 2021 Oct 28;12(45):15061-15066. doi: 10.1039/d1sc04288b. eCollection 2021 Nov 24.
3
Copper-Promoted Conjugate Addition of Carboxylic Acids to Ethenesulfonyl Fluoride (ESF) for Constructing Aliphatic Sulfonyl Fluorides.铜促进羧酸与乙烯基磺酰氟（ESF）的共轭加成反应以构建脂肪族磺酰氟。
ACS Omega. 2021 Sep 27;6(40):25972-25981. doi: 10.1021/acsomega.1c02804. eCollection 2021 Oct 12.
4
Copper-catalyzed enantioselective alkene carboetherification for the synthesis of saturated six-membered cyclic ethers.铜催化的对映选择性烯烃碳环醚化反应合成饱和六元环醚。
Chem Commun (Camb). 2021 Sep 30;57(78):10099-10102. doi: 10.1039/d1cc03515k.
5
Enantio- and Regioselective Palladium(II)-Catalyzed Dioxygenation of (Aza-)Alkenols.钯（II）催化（氮杂）烯醇的对映选择性和区域选择性双氧化反应
Angew Chem Int Ed Engl. 2021 Sep 27;60(40):21723-21727. doi: 10.1002/anie.202109312. Epub 2021 Sep 6.
6
Copper-catalyzed enantioselective synthesis of bridged bicyclic ketals from 1,1-disubstituted-4-methylene-1,6-hexanediols and related alkenols.铜催化的 1,1-二取代-4-亚甲基-1,6-己二醇和相关烯丙醇构建桥环双环缩酮的对映选择性合成。
Chem Commun (Camb). 2021 Jan 5;57(1):105-108. doi: 10.1039/d0cc06404a.
7
Selenophosphoramide-catalyzed diamination and oxyamination of alkenes.硒代磷酰胺催化的烯烃双胺化和氧胺化反应。
Chem Sci. 2019 Dec 26;11(6):1677-1682. doi: 10.1039/c9sc05335b. eCollection 2020 Feb 14.
8
Efficient Stereoselective Carbocyclization to -1,4-Disubstituted Heterocycles Enabled by Dual Pd/Electron Transfer Mediator (ETM) Catalysis.双钯/电子转移介体（ETM）催化促进的高效立体选择性碳环化反应合成 -1,4-二取代杂环化合物。
J Am Chem Soc. 2020 Mar 25;142(12):5751-5759. doi: 10.1021/jacs.9b13700. Epub 2020 Mar 13.
9
Ligand Controlled Ir-Catalyzed Regiodivergent Oxyamination of Unactivated Alkenes.配体控制的铱催化非活化烯烃的区域选择性氧胺化反应。
J Am Chem Soc. 2019 Jul 31;141(30):11864-11869. doi: 10.1021/jacs.9b06366. Epub 2019 Jul 16.
10
Stereoselective and Regioselective Synthesis of Heterocycles via Copper-Catalyzed Additions of Amine Derivatives and Alcohols to Alkenes.通过铜催化的胺衍生物和醇对烯烃的加成反应进行的立体选择性和区域选择性杂环合成。
J Org Chem. 2017 Nov 3;82(21):11311-11325. doi: 10.1021/acs.joc.7b02072. Epub 2017 Sep 29.
本文引用的文献
1
Copper-catalyzed intramolecular alkene carboetherification: synthesis of fused-ring and bridged-ring tetrahydrofurans.铜催化的内环烯烃碳醚化反应：稠环和桥环四氢呋喃的合成。
J Am Chem Soc. 2012 Jul 25;134(29):12149-56. doi: 10.1021/ja3034075. Epub 2012 Jul 5.
2
A general, enantioselective synthesis of protected morpholines and piperazines.一种通用的、对映选择性的保护吗啉和哌嗪的合成方法。
Org Lett. 2012 Jun 1;14(11):2910-3. doi: 10.1021/ol301203z. Epub 2012 May 22.
3
Intramolecular Pd(II)-catalyzed aerobic oxidative amination of alkenes: synthesis of six-membered N-heterocycles.分子内 Pd(II)-催化的烯烃的有氧氧化氨化：六元 N-杂环的合成。
Org Lett. 2012 Mar 2;14(5):1234-7. doi: 10.1021/ol300030w. Epub 2012 Feb 22.
4
Evidence for alkene cis-aminocupration, an aminooxygenation case study: kinetics, EPR spectroscopy, and DFT calculations.烯烃顺式-氨基铜化反应的证据，一个氨氧化案例研究：动力学、EPR 光谱和 DFT 计算。
Chemistry. 2012 Feb 6;18(6):1711-26. doi: 10.1002/chem.201101703. Epub 2012 Jan 11.
5
Regioselective base-free intermolecular aminohydroxylations of hindered and functionalized alkenes.区域选择性无碱分子间氨羟化反应在受阻和官能化烯烃上的应用。
J Org Chem. 2012 Jan 20;77(2):1208-14. doi: 10.1021/jo202375a. Epub 2012 Jan 4.
6
I2-mediated diversity oriented diastereoselective synthesis of amino acid derived trans-2,5-disubstituted morpholines, piperazines, and thiomorpholines.I2 介导的多样性导向的非对映选择性合成氨基酸衍生的反式 2,5-二取代吗啉、哌嗪和硫代吗啉。
ACS Comb Sci. 2012 Jan 9;14(1):1-4. doi: 10.1021/co200129t. Epub 2011 Dec 6.
7
Copper(I) catalyzed regioselective asymmetric alkoxyamination of aryl enamide derivatives.铜（I）催化的芳基烯酰胺衍生物的区域选择性不对称烷氧基胺化反应。
Org Lett. 2011 Nov 4;13(21):5792-5. doi: 10.1021/ol202367d. Epub 2011 Oct 5.
8
Stereoselective Copper-Catalyzed Intramolecular Alkene Aminooxygenation: Effects of Substrate and Ligand Structure on Selectivity.立体选择性铜催化分子内烯烃氨氧化反应：底物和配体结构对选择性的影响
European J Org Chem. 2011 Jul 1;2001(20-21):3679-3684. doi: 10.1002/ejoc.201100444.
9
Metal-free oxyaminations of alkenes using hydroxamic acids.使用羟胺酸实现烯烃的无金属氧胺化反应。
J Am Chem Soc. 2011 Aug 3;133(30):11402-5. doi: 10.1021/ja204255e. Epub 2011 Jul 12.
10
Copper-catalyzed annulative amination of ortho-alkynylphenols with hydroxylamines: synthesis of 3-aminobenzofurans by umpolung amination strategy.铜催化邻炔基苯酚与羟胺的环化胺化反应：反极性胺化策略合成 3-氨基苯并呋喃。
Org Lett. 2011 May 6;13(9):2395-7. doi: 10.1021/ol200651r. Epub 2011 Mar 30.
Zotero 插件