L-脯氨酸在离子液体[bmim]PF6中催化硫酚对α,β-不饱和化合物，特别是α-烯酮的迈克尔加成反应。
L-proline catalyzed Michael additions of thiophenols to alpha,beta-unsaturated compounds, particularly alpha-enones, in the ionic liquid [bmim]PF6.
作者信息
Kotrusz Peter, Toma Stefan
机构信息
SYNKOLA, s.r.o., SK-842 15 Bratislava, Slovakia.
出版信息
Molecules. 2006 Mar 17;11(2):197-205. doi: 10.3390/11020197.
Abstract
L-proline catalyzed additions of 13 different thiols to 11 different alpha-enone Michael acceptors in [bmim] PF(6 )are reported. Reasonable to high yields of the reaction products were isolated in most cases.
摘要
据报道，在[bmim]PF(6)中，L-脯氨酸催化13种不同的硫醇与11种不同的α-烯酮迈克尔受体发生加成反应。在大多数情况下，反应产物的产率适中至高。
相似文献
1
L-proline catalyzed Michael additions of thiophenols to alpha,beta-unsaturated compounds, particularly alpha-enones, in the ionic liquid [bmim]PF6.
Molecules. 2006 Mar 17;11(2):197-205. doi: 10.3390/11020197.
2
Michael addition of thiols to alpha-enones in ionic liquids with and without organocatalysts.
Org Biomol Chem. 2006 Apr 7;4(7):1420-4. doi: 10.1039/b516289k. Epub 2006 Mar 6.
3
Ruthenium(III) chloride catalyzed acylation of alcohols, phenols, and thiols in room temperature ionic liquids.
Molecules. 2009 Sep 10;14(9):3528-37. doi: 10.3390/molecules14093528.
4
An improved procedure for the three-component synthesis of highly substituted pyridines using ionic liquid.
J Org Chem. 2007 Apr 13;72(8):3152-4. doi: 10.1021/jo070015g. Epub 2007 Mar 17.
5
Prolinethiol ether catalysis in an asymmetric Michael reaction: solvent-free synthesis of functionalized monohaloalkenes.
J Org Chem. 2013 Feb 1;78(3):1254-9. doi: 10.1021/jo302288z. Epub 2013 Jan 10.
6
Green protocol for conjugate addition of thiols to alpha,beta-unsaturated ketones using a [bmim]PF6/H2O system.
J Org Chem. 2003 Sep 5;68(18):7098-100. doi: 10.1021/jo034335l.
7
CuI-nanoparticles-catalyzed selective synthesis of phenols, anilines, and thiophenols from aryl halides in aqueous solution.
J Org Chem. 2011 Apr 1;76(7):2296-300. doi: 10.1021/jo102506x. Epub 2011 Feb 28.
8
Synthesis of novel estrone analogs by incorporation of thiophenols via conjugate addition to an enone side chain.
Steroids. 2013 Nov;78(11):1119-25. doi: 10.1016/j.steroids.2013.07.005. Epub 2013 Jul 27.
9
Trace amount Cu (ppm)-catalyzed intramolecular cyclization of 2-(gem-dibromovinyl)phenols(thiophenols) to 2-bromobenzofurans(thiophenes).
Org Biomol Chem. 2013 Jun 28;11(24):4095-101. doi: 10.1039/c3ob40531a.
10
Ligand-free copper-catalyzed C-S coupling of aryl iodides and thiols.
J Org Chem. 2008 Jul 18;73(14):5625-8. doi: 10.1021/jo800491k. Epub 2008 Jun 21.
引用本文的文献
1
An efficient, mild and metal free l-proline catalyzed construction of fused pyrimidines under microwave conditions in water.
RSC Adv. 2019 Feb 4;9(7):3755-3763. doi: 10.1039/c8ra07517d. eCollection 2019 Jan 25.
2
Metal-Free Construction of Fused Pyrimidines via Consecutive C-C and C-N Bond Formation in Water.
ACS Omega. 2018 Nov 7;3(11):15035-15042. doi: 10.1021/acsomega.8b01993. eCollection 2018 Nov 30.
3
Non-Covalent Supported of l-Proline on Graphene Oxide/Fe₃O₄ Nanocomposite: A Novel, Highly Efficient and Superparamagnetically Separable Catalyst for the Synthesis of Bis-Pyrazole Derivatives.
Molecules. 2018 Feb 5;23(2):330. doi: 10.3390/molecules23020330.
本文引用的文献
1
Enantioselective chemo- and bio-catalysis in ionic liquids.
Chem Commun (Camb). 2004 May 7(9):1033-43. doi: 10.1039/b309027b. Epub 2003 Oct 8.
2
Green protocol for conjugate addition of thiols to alpha,beta-unsaturated ketones using a [bmim]PF6/H2O system.
J Org Chem. 2003 Sep 5;68(18):7098-100. doi: 10.1021/jo034335l.
3
A general, Brønsted acid-catalyzed hetero-Michael addition of nitrogen, oxygen, and sulfur nucleophiles.
Org Lett. 2003 Jun 12;5(12):2141-4. doi: 10.1021/ol034596h.
4
Ionic liquid (molten salt) phase organometallic catalysis.
Chem Rev. 2002 Oct;102(10):3667-92. doi: 10.1021/cr010338r.
5
Catalytic reactions in ionic liquids.
Chem Commun (Camb). 2001 Dec 7(23):2399-407. doi: 10.1039/b107270f.
6
Metal-catalyzed carbon-sulfur bond formation.
Chem Rev. 2000 Aug 9;100(8):3205-20. doi: 10.1021/cr9902749.
7
Enantioselective Organocatalysis.
Angew Chem Int Ed Engl. 2001 Oct 15;40(20):3726-3748. doi: 10.1002/1521-3773(20011015)40:20<3726::aid-anie3726>3.0.co;2-d.
8
The Application of L-Proline as an Enzyme Mimic and Further New Asymmetric Syntheses Using Small Organic Molecules as Chiral Catalysts.
Angew Chem Int Ed Engl. 2001 Feb 2;40(3):529-532.
Zotero 插件