ArticleMolecules (Basel, Switzerland)2021
Synthesis of Novel Crown Ether-Squaramides and Their Application as Phase-Transfer Catalysts.
Zsuzsanna Fehér, Dóra Richter, Sándor Nagy, Péter Bagi, Zsolt Rapi, András Simon, László Drahos, Péter Huszthy, Péter Bakó, József Kupai
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In one paragraphArticle in Molecules (Basel, Switzerland), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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10 authors.
Zsuzsanna FehérDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szent Gellért tér 4, H-1111 Budapest, Hungary.
Dóra RichterDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szent Gellért tér 4, H-1111 Budapest, Hungary.
Sándor NagyDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szent Gellért tér 4, H-1111 Budapest, Hungary.ORCID 0000-0001-6251-5382 Péter BagiDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szent Gellért tér 4, H-1111 Budapest, Hungary.ORCID 0000-0002-9043-6435 Zsolt RapiDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szent Gellért tér 4, H-1111 Budapest, Hungary.ORCID 0000-0002-6035-5482 András SimonDepartment of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Szent Gellért tér 4, H-1111 Budapest, Hungary.
László DrahosMS Proteomics Research Group, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar Tudósok körútja 2, H-1117 Budapest, Hungary.ORCID 0000-0001-9589-6652 Péter HuszthyDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szent Gellért tér 4, H-1111 Budapest, Hungary.ORCID 0000-0001-7305-3312 Péter BakóDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szent Gellért tér 4, H-1111 Budapest, Hungary.
József KupaiDepartment of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szent Gellért tér 4, H-1111 Budapest, Hungary.ORCID 0000-0002-4212-4517 Funding
Gedeon Richter (Hungary) Talentum PhD Scholarship of Zsuzsanna FeherHungarian Academy of Sciences János Bolyai scholarhip of Jozsef KupaiHungarian Scientific Research Fund FK138037Hungarian Scientific Research Fund K128473Ministry of Human Capacities ÚNKP-20-3-II-BME-325Ministry of Human Capacities ÚNKP-20-5-BME-322Ministry of Human Capacities ÚNKP-21-2-I-BME-209Servier (France) PhD Scholarship of Sandor Nagy
6 · The paper itselfAbstract
This work presents the synthesis of six new phase-transfer organocatalysts in which the squaramide unit is directly linked to the nitrogen atom of an aza-crown ether. Four chiral skeletons, namely hydroquinine, quinine, cinchonine (cinchonas), and α-d-glucopyranoside were responsible for the asymmetric construction of an all-carbon quaternary stereogenic center in α-alkylation and Michael addition reactions of malonic esters. We investigated the effects of these different chiral units and that of crown ethers with different sizes on catalytic activity and enantioselectivity. During extensive parameter investigations, both conventional and emerging green solvents were screened, providing valuable α,α-disubstituted malonic ester derivatives with excellent yields (up to 98%).
Indexed as
allylationamino acidsasymmetric catalysiscarbohydratescrown compoundsenantioselectivityphase-transfer catalysis
Identifiers
PMID34770950
PMCPMC8588334
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