Calixarene-based chiral phase-transfer catalysts derived from cinchona alkaloids for enantioselective synthesis of α-amino acids

Bozkurt, Selahattin; Durmaz, Mustafa; Yılmaz, Mustafa; Sirit, Abdulkadir

doi:10.1016/j.tetasy.2008.02.006

Cited by 57 publications

(24 citation statements)

References 72 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Sirit and co-workers used three calixarene-based quaternary ammonium salts of Cinchona alkaloids in benzylation of glycine imine ethyl ester to achieve up to 57% enantioselectivity. 103 N ajera and co-workers have used polymer-supported chiral ammonium salts 176 (Fig. 20) derived from cinchonidine and quinine as phase-transfer catalysts in the asymmetric benzylation of glycine imine isopropyl ester 177.…”

Section: Alkylation Of Glycine Imine Estersmentioning

confidence: 99%

Recent applications of Cinchona alkaloids and their derivatives as catalysts in metal-free asymmetric synthesis

2011

View full text Add to dashboard Cite

Section: Alkylation Of Glycine Imine Estersmentioning

confidence: 99%

Recent applications of Cinchona alkaloids and their derivatives as catalysts in metal-free asymmetric synthesis

2011

View full text Add to dashboard Cite

“…[9] Die asymmetrische Benzylierung von 7 mit diesen Katalysatoren lieferte das Produkt 8 mit mittleren bis guten Enantioselektivitäten (Schema 5).…”

Section: Asymmetrische Synthese Von A-aminosäurenunclassified

Neue Entwicklungen bei asymmetrischen Phasentransferreaktionen

2013

View full text Add to dashboard Cite

Die Phasentransferkatalyse bildet eine effiziente Grundlage zur Einführung praktischer Methoden in die organische Synthese, denn sie bietet mehrere Vorteile wie einfache Handhabung, milde Reaktionsbedingungen, die Eignung für großtechnische Synthesen und ein umweltfreundliches Reaktionssystem. Seit den wegweisenden Arbeiten zu hoch enantioselektiven Alkylierungen mit chiralen Phasentransferkatalysatoren ist dieses Forschungsgebiet im Hinblick auf eine umweltverträgliche, nachhaltige Chemie von Interesse, und in den vergangenen Jahrzehnten, vor allem in den letzten Jahren, wurden zahlreiche asymmetrische, durch chirale Oniumsalze und Kronenether katalysierte Umwandlungen für die Synthese wertvoller organischer Verbindungen entwickelt.

show abstract

“…In this context, calixarenes are ideal supramolecular macrocyclic scaffolds for the design of molecular receptors and organocatalysts due to their unique and tunable molecular architecture together with the ease of functionalization on the lower and upper rims [24–28]. Interestingly, their hydrophobic cavity also exhibits phase transfer catalytic function [29]. By attaching different pendants with catalytic ability to the scaffolds, this may offer us the opportunity to improve the green aspect of many reactions both in organic and aqueous medium [30].…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Michael addition reactions catalyzed by calix[4]thiourea cyclohexanediamine derivatives

Tong

Chen

et al. 2018

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

A number of upper rim-functionalized calix[4]thiourea cyclohexanediamine derivatives have been designed, synthesized and used as catalysts for enantioselective Michael addition reactions between nitroolefins and acetylacetone. The optimal catalyst 2 with a mono-thiourea group exhibited good performance in the presence of water/toluene (v/v = 1:2). Under the optimal reaction conditions, high yields of up to 99% and moderate to good enantioselectivities up to 94% ee were achieved. Detailed experiments clearly showed that the upper rim-functionalized hydrophobic calixarene scaffold played an important role in cooperation with the catalytic center to the good reactivities and enantioselectivities.

show abstract

Calixarene-based chiral phase-transfer catalysts derived from cinchona alkaloids for enantioselective synthesis of α-amino acids

Cited by 57 publications

References 72 publications

Recent applications of Cinchona alkaloids and their derivatives as catalysts in metal-free asymmetric synthesis

Recent applications of Cinchona alkaloids and their derivatives as catalysts in metal-free asymmetric synthesis

Neue Entwicklungen bei asymmetrischen Phasentransferreaktionen

Asymmetric Michael addition reactions catalyzed by calix[4]thiourea cyclohexanediamine derivatives

Contact Info

Product

Resources

About