Rhodium-catalyzed asymmetric intramolecular hydroamination of unactivated alkenes.
作者信息
Shen Xiaoqiang, Buchwald Stephen L
机构信息
Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge MA 02139, USA.
出版信息
Angew Chem Int Ed Engl. 2010;49(3):564-7. doi: 10.1002/anie.200905402.
Abstract
摘要
相似文献
1
Rhodium-catalyzed asymmetric intramolecular hydroamination of unactivated alkenes.
Angew Chem Int Ed Engl. 2010;49(3):564-7. doi: 10.1002/anie.200905402.
2
Mild, rhodium-catalyzed intramolecular hydroamination of unactivated terminal and internal alkenes with primary and secondary amines.
J Am Chem Soc. 2008 Feb 6;130(5):1570-1. doi: 10.1021/ja710126x. Epub 2008 Jan 10.
3
Rhodium-catalyzed sequential allylic amination and olefin hydroacylation reactions: enantioselective synthesis of seven-membered nitrogen heterocycles.
Angew Chem Int Ed Engl. 2014 Apr 1;53(14):3688-92. doi: 10.1002/anie.201310354. Epub 2014 Mar 3.
4
Stereoselective rhodium-catalyzed amination of alkenes.
Org Lett. 2011 Oct 21;13(20):5460-3. doi: 10.1021/ol2021516. Epub 2011 Sep 15.
5
A simple and efficient iron-catalyzed intramolecular hydroamination of unactivated olefins.
Angew Chem Int Ed Engl. 2006 Apr 28;45(18):2938-41. doi: 10.1002/anie.200503789.
6
Highly regioselective isomerization-hydroaminomethylation of internal olefins catalyzed by Rh complex with Tetrabi-type phosphorus ligands.
Org Lett. 2012 Jan 6;14(1):102-5. doi: 10.1021/ol202848a. Epub 2011 Dec 13.
7
Intramolecular hydroamination of unbiased and functionalized primary aminoalkenes catalyzed by a rhodium aminophosphine complex.
J Am Chem Soc. 2010 Oct 6;132(39):13813-22. doi: 10.1021/ja1052126.
8
Rhodium phosphine-π-arene intermediates in the hydroamination of alkenes.
J Am Chem Soc. 2011 Mar 2;133(8):2772-82. doi: 10.1021/ja1057949. Epub 2011 Feb 10.
9
Enantio- and regioselective CuH-catalyzed hydroamination of alkenes.
J Am Chem Soc. 2013 Oct 23;135(42):15746-9. doi: 10.1021/ja4092819. Epub 2013 Oct 15.
10
Chiral sulfoxide-olefin ligands: completely switchable stereoselectivity in rhodium-catalyzed asymmetric conjugate additions.
Angew Chem Int Ed Engl. 2011 Aug 8;50(33):7681-5. doi: 10.1002/anie.201102586. Epub 2011 Jul 1.
引用本文的文献
1
Catalytic enantioselective intramolecular hydroamination of alkenes using chiral aprotic cyclic urea ligand on manganese (II).
Nat Commun. 2024 Aug 5;15(1):6647. doi: 10.1038/s41467-024-50757-4.
2
Green Catalytic Synthesis of Ethylenediamine from Ethylene Glycol and Monoethanolamine: A Review.
ACS Omega. 2024 Apr 16;9(17):18747-18756. doi: 10.1021/acsomega.4c00709. eCollection 2024 Apr 30.
3
A redox-enabled strategy for intramolecular hydroamination.
Chem Sci. 2022 May 30;13(24):7264-7268. doi: 10.1039/d2sc00481j. eCollection 2022 Jun 22.
4
External electric field: a new catalytic strategy for the anti-Markovnikov hydrohydrazination of parent hydrazine.
RSC Adv. 2021 Mar 22;11(19):11595-11605. doi: 10.1039/d1ra01037a. eCollection 2021 Mar 16.
5
Design, scope and mechanism of highly active and selective chiral NHC-iridium catalysts for the intramolecular hydroamination of a variety of unactivated aminoalkenes.
Chem Sci. 2021 Feb 1;12(10):3751-3767. doi: 10.1039/d0sc05884j.
6
Rare-Earth-Metal-Catalyzed Kinetic Resolution of Chiral Aminoalkenes via Hydroamination: The Effect of the Silyl Substituent of the Binaphtholate Ligand on Resolution Efficiency.
European J Org Chem. 2019 Apr 24;2019(15):2592-2601. doi: 10.1002/ejoc.201900107. Epub 2019 Mar 13.
7
3-Aryl-2,5-Dihydropyrroles via Catalytic Carbonyl-Olefin Metathesis.
ACS Catal. 2018 Mar 2;8(3):2006-2011. doi: 10.1021/acscatal.7b03769. Epub 2018 Jan 18.
8
Hydroamination versus Allylic Amination in Iridium-Catalyzed Reactions of Allylic Acetates with Amines: 1,3-Aminoalcohols via Ester-Directed Regioselectivity.
J Am Chem Soc. 2018 Jul 25;140(29):9087-9090. doi: 10.1021/jacs.8b05683. Epub 2018 Jul 10.
9
Synthetic and Computational Studies on the Rhodium-Catalyzed Hydroamination of Aminoalkenes.
ACS Catal. 2016 Sep 2;6:5651-5665. doi: 10.1021/acscatal.6b01320. Epub 2016 Jul 13.
10
Rhodium-catalysed syn-carboamination of alkenes via a transient directing group.
Nature. 2015 Nov 5;527(7576):86-90. doi: 10.1038/nature15691. Epub 2015 Oct 21.
本文引用的文献
1
The enantioselective intramolecular aminative functionalization of unactivated alkenes, dienes, allenes and alkynes for the synthesis of chiral nitrogen heterocycles.
Org Biomol Chem. 2009;7(15):3009-3019. doi: 10.1039/B907743J.
2
Palladium-catalyzed asymmetric dearomatization of naphthalene derivatives.
J Am Chem Soc. 2009 May 20;131(19):6676-7. doi: 10.1021/ja9025193.
3
Intermolecular hydroamination of ethylene and 1-alkenes with cyclic ureas catalyzed by achiral and chiral gold(I) complexes.
J Am Chem Soc. 2009 Apr 22;131(15):5372-3. doi: 10.1021/ja9001162.
4
Zirconium Bis(Amido) Catalysts for Asymmetric Intramolecular Alkene Hydroamination.
Organometallics. 2006 Sep 25;25(20):4731-4733. doi: 10.1021/om0606791.
5
Hydroamination: direct addition of amines to alkenes and alkynes.
Chem Rev. 2008 Sep;108(9):3795-892. doi: 10.1021/cr0306788. Epub 2008 Aug 26.
6
Intermolecular, catalytic asymmetric hydroamination of bicyclic alkenes and dienes in high yield and enantioselectivity.
J Am Chem Soc. 2008 Sep 17;130(37):12220-1. doi: 10.1021/ja803523z. Epub 2008 Aug 21.
7
Biaryl phosphane ligands in palladium-catalyzed amination.
Angew Chem Int Ed Engl. 2008;47(34):6338-61. doi: 10.1002/anie.200800497.
8
Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions employing dialkylbiaryl phosphine ligands.
Acc Chem Res. 2008 Nov 18;41(11):1461-73. doi: 10.1021/ar800036s.
9
Mild, rhodium-catalyzed intramolecular hydroamination of unactivated terminal and internal alkenes with primary and secondary amines.
J Am Chem Soc. 2008 Feb 6;130(5):1570-1. doi: 10.1021/ja710126x. Epub 2008 Jan 10.
10
Asymmetric hydroamination of non-activated carbon-carbon multiple bonds.
Dalton Trans. 2007 Nov 28(44):5105-18. doi: 10.1039/b711126f. Epub 2007 Sep 7.
Zotero 插件