新型双功能磺胺催化对映选择性共轭加成反应。
Novel bifunctional sulfonamides catalyze an enantioselective conjugate addition.
作者信息
McGarraugh Patrick G, Brenner Stacey E
机构信息
Department of Chemistry, Brooklyn College and the City University of New York, 2900 Bedford Avenue, Brooklyn, NY 11210, USA.
出版信息
Tetrahedron. 2009 Jan 10;65(2):449-455. doi: 10.1016/j.tet.2008.11.027.
Abstract
A new bifunctional organocatalyst with a novel structural and functional motif has been developed. This bifunctional sulfonamide organocatalyst was used in the conjugate addition of 1,3-dicarbonyl compounds (13) to β-nitrostyrenes (12). Yields up to 91% and enantiomeric excesses up to 79% were obtained in this reaction. This catalyst activates both 13 via its basic moiety and 12 through hydrogen bonding.
摘要
一种具有新型结构和功能基序的新型双功能有机催化剂已被开发出来。这种双功能磺酰胺有机催化剂被用于1,3 - 二羰基化合物（13）与β-硝基苯乙烯（12）的共轭加成反应。该反应获得了高达91%的产率和高达79%的对映体过量。这种催化剂通过其碱性部分活化13，并通过氢键作用活化12。
相似文献
1
Novel bifunctional sulfonamides catalyze an enantioselective conjugate addition.
Tetrahedron. 2009 Jan 10;65(2):449-455. doi: 10.1016/j.tet.2008.11.027.
2
New bifunctional 1,3-diamine organocatalysts derived from (+)-camphoric acid for asymmetric Michael addition of 1,3-dicarbonyl compounds to nitroolefins.
Chirality. 2022 May;34(5):782-795. doi: 10.1002/chir.23424. Epub 2022 Feb 15.
3
The synthesis of chiral β-naphthyl-β-sulfanyl ketones via enantioselective sulfa-Michael reaction in the presence of a bifunctional cinchona/sulfonamide organocatalyst.
Beilstein J Org Chem. 2021 Feb 18;17:494-503. doi: 10.3762/bjoc.17.43. eCollection 2021.
4
Asymmetric synthesis of highly functionalized tetrahydropyrans via a one-pot organocatalytic Michael/Henry/ketalization sequence.
Org Lett. 2014 Jul 18;16(14):3636-9. doi: 10.1021/ol501236a. Epub 2014 Jun 27.
5
Synthesis and characterization of binary-complex models of ureas and 1,3-dicarbonyl compounds: deeper insights into reaction mechanisms using snap-shot structural analysis.
J Org Chem. 2014 Feb 21;79(4):1805-17. doi: 10.1021/jo4028775. Epub 2014 Feb 4.
6
Enantioselective organocatalytic Michael-hemiketalization catalyzed by a trans-bifunctional indane thiourea catalyst.
Org Biomol Chem. 2011 May 21;9(10):3691-7. doi: 10.1039/c1ob05404j. Epub 2011 Apr 11.
7
Asymmetric Michael Additions of 4-Hydroxycoumarin to β-Nitrostyrenes with Chiral, Bifunctional Hydrogen-Bonding Catalysts.
J Org Chem. 2016 Mar 4;81(5):1762-8. doi: 10.1021/acs.joc.5b02167. Epub 2016 Feb 12.
8
Chiral Sodium Glycerophosphate Catalyst for Enantioselective Michael Reactions of Chalcones.
Molecules. 2024 Oct 8;29(19):4763. doi: 10.3390/molecules29194763.
9
Creation through immobilization: a new family of high performance heterogeneous bifunctional iminophosphorane (BIMP) superbase organocatalysts.
Org Lett. 2014 Dec 19;16(24):6294-7. doi: 10.1021/ol5029942. Epub 2014 Dec 2.
10
Enantioselective conjugate addition of nitro compounds to α,β-unsaturated ketones: an experimental and computational study.
Chemistry. 2011 May 16;17(21):5931-8. doi: 10.1002/chem.201100241. Epub 2011 Apr 15.
引用本文的文献
1
Chiral Thioureas-Preparation and Significance in Asymmetric Synthesis and Medicinal Chemistry.
Molecules. 2020 Jan 18;25(2):401. doi: 10.3390/molecules25020401.
2
Exploring the potential of diarylacetylenediols as hydrogen bonding catalysts.
J Org Chem. 2013 Sep 6;78(17):8340-53. doi: 10.1021/jo400926n. Epub 2013 Aug 14.
本文引用的文献
1
Lessons from nature: biomimetic organocatalytic carbon-carbon bond formations.
J Org Chem. 2008 Oct 17;73(20):7857-70. doi: 10.1021/jo801374j. Epub 2008 Sep 9.
2
Asymmetric aminocatalysis--gold rush in organic chemistry.
Angew Chem Int Ed Engl. 2008;47(33):6138-71. doi: 10.1002/anie.200705523.
3
Kinetic resolution of racemic carboxylic acids by an L-histidine-derived sulfonamide-induced enantioselective esterification reaction.
Org Lett. 2008 Aug 7;10(15):3191-4. doi: 10.1021/ol801007m. Epub 2008 Jun 27.
4
Asymmetric organocatalysis: from infancy to adolescence.
Angew Chem Int Ed Engl. 2008;47(25):4638-60. doi: 10.1002/anie.200704684.
5
Bifunctional organocatalyst for methanolytic desymmetrization of cyclic anhydrides: increasing enantioselectivity by catalyst dilution.
Chem Commun (Camb). 2008 Mar 14(10):1208-10. doi: 10.1039/b719811f. Epub 2008 Feb 6.
6
Enantioselective, organocatalytic oxy-michael addition to gamma/delta-hydroxy-alpha,beta-enones: boronate-amine complexes as chiral hydroxide synthons.
J Am Chem Soc. 2008 Jan 9;130(1):46-8. doi: 10.1021/ja076802c. Epub 2007 Dec 13.
7
Small-molecule H-bond donors in asymmetric catalysis.
Chem Rev. 2007 Dec;107(12):5713-43. doi: 10.1021/cr068373r.
8
Stronger Brønsted acids.
Chem Rev. 2007 Dec;107(12):5744-58. doi: 10.1021/cr068374j. Epub 2007 Nov 6.
9
Enantioselective hydroxylation of nitroalkenes: an organocatalytic approach.
Chem Commun (Camb). 2007 Sep 21(35):3646-8. doi: 10.1039/b707844g. Epub 2007 Jun 28.
10
Scope and mechanism of enantioselective Michael additions of 1,3-dicarbonyl compounds to nitroalkenes catalyzed by nickel(II)-diamine complexes.
J Am Chem Soc. 2007 Sep 19;129(37):11583-92. doi: 10.1021/ja0735913. Epub 2007 Aug 24.
Zotero 插件