Synthesis of Novel Crown Ether-Squaramides and Their Application as Phase-Transfer Catalysts

Autor: Zsuzsanna Fehér, Dóra Richter, Sándor Nagy, Péter Bagi, Zsolt Rapi, András Simon, László Drahos, Péter Huszthy, Péter Bakó, József Kupai
Jazyk: angličtina
Rok vydání: 2021
Předmět:
Zdroj: Molecules, Vol 26, Iss 21, p 6542 (2021)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/molecules26216542
Popis: 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%).
Databáze: Directory of Open Access Journals
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