Show simple item record

Asymmetric Friedel–Crafts Alkylation of Indoles Catalyzed by Chiral Aziridine-Phosphines

dc.contributor.authorBuchcic, Aleksandra
dc.contributor.authorZawisza, Anna
dc.contributor.authorLeśniak, Stanisław
dc.contributor.authorRachwalski, Michał
dc.date.accessioned2021-10-26T08:30:09Z
dc.date.available2021-10-26T08:30:09Z
dc.date.issued2020
dc.identifier.citationBuchcic, A.; Zawisza, A.; Leśniak, S.; Rachwalski, M. Asymmetric Friedel–Crafts Alkylation of Indoles Catalyzed by Chiral Aziridine-Phosphines. Catalysts 2020, 10, 971. https://doi.org/10.3390/catal10090971pl_PL
dc.identifier.issn2073-4344
dc.identifier.urihttp://hdl.handle.net/11089/39553
dc.description.abstractOver the course of the present studies, a series of optically pure phosphines functionalized by chiral aziridines was synthesized in reasonable/good chemical yields. Their catalytic activity was checked in the enantioselective Friedel–Crafts alkylation of indoles by β-nitrostyrene in the presence of a copper(I) trifluoromethanesulfonate benzene complex. The corresponding Friedel–Crafts products were achieved efficiently in terms of chemical yield and enantioselectivity (up to 85% in some cases).pl_PL
dc.description.sponsorshipThis research was funded by the National Science Centre (NCN) (Grant No. 2016/21/B/ST5/00421 for M.R.).pl_PL
dc.language.isoenpl_PL
dc.publisherMDPIpl_PL
dc.relation.ispartofseriesCatalysts;10(9)
dc.rightsUznanie autorstwa 4.0 Międzynarodowe*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.subjectasymmetric transformationspl_PL
dc.subjectchiral aziridinyl-phosphinespl_PL
dc.subjectenantioselective Friedel–Crafts alkylationpl_PL
dc.subjectstereoselectivitypl_PL
dc.titleAsymmetric Friedel–Crafts Alkylation of Indoles Catalyzed by Chiral Aziridine-Phosphinespl_PL
dc.typeArticlepl_PL
dc.page.number10pl_PL
dc.contributor.authorAffiliationDepartment of Organic and Applied Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Polandpl_PL
dc.contributor.authorAffiliationDepartment of Organic and Applied Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Polandpl_PL
dc.contributor.authorAffiliationDepartment of Organic and Applied Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Polandpl_PL
dc.contributor.authorAffiliationDepartment of Organic and Applied Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Polandpl_PL
dc.referencesDa Gama Oliveira, V.; do Carmo Cardoso, M.F.; da Silva Magalhães Forezi, L. Organocatalysis: A brief overview on its evolution and application. Catalysts 2018, 8, 605.pl_PL
dc.referencesPellissier, H. Asymmetric organocatalysis. Tetrahedron 2007, 63, 9267–9331.pl_PL
dc.referencesKagan, H.B.; Gopalaiah, K. Early history of asymmetric synthesis: Who are the scientists who set up the basic principles and the first experiments. New J. Chem. 2011, 35, 1933–1937.pl_PL
dc.referencesLi, L.; Chen, Z.; Zhang, X.; Jia, Y. Divergent strategy in natural product total synthesis. Chem. Rev. 2018, 118, 3752–3832.pl_PL
dc.referencesShimokawa, J. Divergent strategy in natural product total synthesis. Tetrahedron Lett. 2014, 55, 6156–6162.pl_PL
dc.referencesKrautwald, S.; Carreira, E.M. Stereodivergence in asymmetric catalysis. J. Am. Chem. Soc. 2017, 139, 5627–5639.pl_PL
dc.referencesChoi, J.; Fu, G.C. Catalytic asymmetric synthesis of secondary nitriles via stereoconvergent Negishi arylations and alkenylations of racemic -bromonitriles. J. Am. Chem. Soc. 2012, 134, 9102–9105.pl_PL
dc.referencesKalek, M.; Fu, G.C. Phosphine-catalyzed doubly stereoconvergent -additions of racemic heterocycles to racemic allenoates: The catalytic enantioselective synthesis of protected , -disubstituted -amino acid derivatives. J. Am. Chem. Soc. 2015, 137, 9438–9442.pl_PL
dc.referencesPark, J.K.; Lackey, H.H.; Ondrusek, B.A.; McQuade, D.T. Stereoconvergent synthesis of chiral allylboronates from an E/Z mixture of allylic aryl ethers using a 6-NHC-Cu(I) catalyst. J. Am. Chem. Soc. 2011, 133, 2410–2413.pl_PL
dc.referencesPoulsen, T.B.; Jørgensen, K.A. Catalytic asymmetric Friedel-Crafts alkylation reactions—Copper showed the way. Chem. Rev. 2008, 108, 2903–2915.pl_PL
dc.referencesSingh, P.K.; Bisai, A.; Singh, V.K. Enantioselective Friedel-Crafts alkylation of indoles with nitroalkanes catalyzed by a bis(oxazoline)-Cu(II) complex. Tetrahedron Lett. 2007, 48, 1127–1129.pl_PL
dc.referencesLi, W. Chiral bis(oxazolinyl)thiophenes for enantioselective Cu(II)-catalyzed Friedel-Crafts alkylation of indole derivatives with nitroalkenes. Catal. Lett. 2014, 144, 943–948.pl_PL
dc.referencesLiu, T.-Y.; Cui, H.-L.; Chai, Q.; Long, J.; Li, B.-J.; Wu, Y.; Ding, L.-S.; Chen, Y.-C. Organocatalytic asymmetric Friedel-Crafts alkylation/cascade reactions of naphthols and nitroolefins. Chem. Commun. 2007, 2228–2230.pl_PL
dc.referencesWang, Y.-Q.; Song, J.; Hong, R.; Li, H.; Deng, L. Asymmetric Friedel-Crafts reaction of indoles with imines by an organic catalyst. J. Am. Chem. Soc. 2006, 128, 8156–8157.pl_PL
dc.referencesÖzdemir, H.S.; ¸Sahin, E.; Çakici, M.; Kiliç, H. Asymmetric Friedel-Crafts alkylation of pyrrole with nitroalkenes catalyzed by a copper complex of a bisphenol A-derived Schi base. Tetrahedron 2015, 71, 2882–2890.pl_PL
dc.referencesKim, H.Y.; Kim, S.; Oh, K. Orthogonal enantioselectivity approaches using homogeneous and heterogeneous catalyst systems: Friedel-Crafts alkylation of indole. Angew. Chem. Int. Ed. 2010, 49, 4476–4478.pl_PL
dc.referencesLiu, J.; Gong, L.; Meggers, E. Asymmetric Friedel-Crafts alkylation of indoles with 2-nitro-3-arylacrylates catalyzed by a metal-templated hydrogen bonding catalyst. Tetrahedron Lett. 2015, 56, 4653–4656.pl_PL
dc.referencesKaushik, N.K.; Kaushik, N.; Attri, P.; Kumar, N.; Kim, C.H.; Verma, A.K.; Choi, E.H. Biomedical importance of indoles. Molecules 2013, 18, 6620–6662.pl_PL
dc.referencesSakamoto, T.; Itoh, J.; Mori, K.; Akiyama, T. Chiral Brønsted acid catalyzed Friedel-Crafts alkylation reaction of indoles with , -unsaturated ketones: Short access to optically active 2- and 3-substituted indole derivatives. Org. Biomol. Chem. 2010, 8, 5448–5454.pl_PL
dc.referencesAli, S.; Wisal, A.; Tahir, M.N.; Ali, A.; Hameed, S.; Ahmed, M.N. One-pot synthesis, crystal structure and antimicrobial activity of 6-benzyl-11-(p-tolyl)-6H-indolo[2,3-b]quinoline. J. Mol. Struct. 2020, 1210, 128035.pl_PL
dc.referencesSansinenea, E.; Martínez, E.F.; Ortiz, A. Organocatalytic synthesis of chiral spirooxindoles with quaternary stereogenic centers. Eur. J. Org. Chem. 2020.pl_PL
dc.referencesHong, S.K.; Park, W.; Park, Y.S. Asymmetric synthesis of 4-aryl dihydroisoquinolin-3-ones and 2-aryl morpholin-3-ones using AgOTf-activated -bromo arylacetate. Tetrahedron 2020, 76, 130841.pl_PL
dc.referencesWang, Z.; Zu, L. Organocatalytic enantioselective direct alkylation of phloroglucinol derivatives: Asymmetric total synthesis of (+)-aflatoxin B2. Chem. Commun. 2019, 5171–5174.pl_PL
dc.referencesYang, H.; Tang, W. E cient enantioselective syntheses of chiral natural products facilitated by ligand design. Chem. Rec. 2020, 20, 23–40.pl_PL
dc.referencesKhatri, H.R.; Carney, N.; Rutkoski, R.; Bhattarai, B.; Nagorny, P. Recent progress in steroid synthesis triggered by the emergence of new catalytic methods. Eur. J. Org. Chem. 2020, 7, 755–776.pl_PL
dc.referencesZhao, Y.-L.; Lou, Q.-X.; Wang, L.-S.; Hu, W.-H.; Zhao, J.-L. Organocatalytic Friedel-Crafts alkylation/Lactonization reaction of naphthols with 3-trifluoroethylidene oxindoles: The asymmetric synthesis of dihydrocoumarins. Angew. Chem. Int. Ed. 2017, 56, 338–342.pl_PL
dc.referencesRoemer, M.; Wild, D.A.; Sobolev, A.N.; Skelton, B.W.; Nealon, G.L.; Piggott, M.J.; Koutsantonis, G.A. Carbon-rich trinuclear octamethylferrocenophanes. Inorg. Chem. 2019, 58, 3789–3799.pl_PL
dc.referencesDo˘gan, Ö.; Ça˘ gli, E. PFAM catalyzed enantioselective diethylzinc addition to imines. Turk. J. Chem. 2015, 39, 290–296.pl_PL
dc.referencesDogan, Ö.; Tan, D. Enantioselective direct aldol reactions promoted by phosphine oxide aziridinyl phosphonate organocatalysts. Tetrahedron Asymmetry 2015, 26, 1348–1353.pl_PL
dc.referencesEröksüz, S.; Dogan, Ö.; Garner, P.P. A new chiral phosphine oxide ligand for enantioselective 1,3-dipolar cycloaddition reactions of azomethine ylides. Tetrahedron Asymmetry 2010, 21, 2535–2541.pl_PL
dc.referencesDogan, Ö.; Isci, M.; Aygun, M. New phosphine oxide aziridinyl phosphonates as chiral Lewis bases for the Abramov-type phosphonylation of aldehydes. Tetrahedron Asymmetry 2013, 24, 562–567.pl_PL
dc.referencesDogan, Ö.; Bulut, A.; Tecimer, M.A. Chiral phosphine oxide aziridinyl phosphonate as a Lewis base catalyst for enantioselective allylsilane addition to aldehydes. Tetrahedron Asymmetry 2015, 26, 966–969.pl_PL
dc.referencesWujkowska, Z.; Zawisza, A.; Le´sniak, S.; Rachwalski, M. Phosphinoyl-aziridines as a new class of chiral catalysts for enantioselective Michael addition. Tetrahedron 2019, 75, 230–235.pl_PL
dc.referencesBuchcic, A.; Zawisza, A.; Le´sniak, S.; Adamczyk, J.; Pieczonka, A.M.; Rachwalski, M. Enantioselective Mannich reaction promoted by chiral phosphinoyl-aziridines. Catalysts 2019, 9, 837.pl_PL
dc.referencesLe´sniak, S.; Rachwalski, M.; Jarzy ´ nski, S.; Obijalska, E. Lactic acid derived aziridinyl alcohols as highly e ective catalysts for asymmetric additions of an organozinc species to aldehydes. Tetrahedron Asymmetry 2013, 24, 1336–1340.pl_PL
dc.referencesPieczonka, A.M.; Le´sniak, S.; Rachwalski, M. Direct asymmetric aldol condensation catalyzed by aziridine semicarbazide zinc(II) complexes. Tetrahedron Lett. 2014, 55, 2373–2375.pl_PL
dc.referencesPieczonka, A.M.; Marciniak, L.; Rachwalski, M.; Le´sniak, S. Enantiodivergent aldol condensation in the presence of aziridine/acid/water systems. Symmetry 2020, 12, 930.pl_PL
dc.referencesCoumbe, T.; Lawrence, N.J.; Muhammad, F. Titanium (IV) catalysis in the reduction of phosphine oxides. Tetrahedron Lett. 1994, 35, 625–628.pl_PL
dc.referencesZhang, T.-X.; Zhang, W.-X.; Luo, M.-M. Metal-free reduction of tertiary phosphine oxides with Hantzsch ester. Chin. Chem. Lett. 2014, 25, 176–178.pl_PL
dc.referencesBusacca, C.A.; Raju, R.; Grinberg, N.; Haddad, N.; James-Jones, P.; Lee, H.; Lorenz, J.C.; Saha, A.; Senanayake, C.H. Reduction of tertiary phosphine oxides with DIBAL-H. J. Org. Chem. 2008, 73, 1524–1531.pl_PL
dc.referencesProvis-Evans, C.B.; Emanuelsson, E.A.C.; Webster, R.L. Rapid metal-free formation of free phosphines from phosphine oxides. Adv. Synth. Catal. 2018, 360, 3999–4004.pl_PL
dc.referencesSowa, S.; Stankeviˇc, M.; Szmigielska, A.; Małuszy´ nska, H.; Kozioł, A.E.; Pietrusiewicz, K.M. Reduction of functionalized tertiary phosphine oxides with BH3. J. Org. Chem. 2015, 80, 1672–1688.pl_PL
dc.referencesZhao, W.; Sun, J. Triflimide (HNTf2) in organic synthesis. Chem. Rev. 2018, 118, 10349–10392.pl_PL
dc.referencesShi, H.; Herron, A.N.; Shao, Y.; Shao, Q.; Yu, J.-Q. Enantioselective remote meta-C–H arylation and alkylation via a chiral transient mediator. Nature 2018, 558, 581–586.pl_PL
dc.identifier.doi10.3390/catal10090971
dc.relation.volume971pl_PL
dc.disciplinenauki chemicznepl_PL


Files in this item

Thumbnail
Name:
license_rdf
Size:
908bytes
Format:
application/rdf+xml
View/Open
Thumbnail
Name:
catalysts-10-00971.pdf
Size:
1.364Mb
Format:
PDF
Description:
Article
View/Open

This item appears in the following Collection(s)

Show simple item record

Uznanie autorstwa 4.0 Międzynarodowe
Except where otherwise noted, this item's license is described as Uznanie autorstwa 4.0 Międzynarodowe