Synthesis of calix[4]arene derivatives bearing chiral pendant groups as ligands for enantioselective catalysis

Gaeta, Carmine; Rosa, Margherita De; Fruilo, Marina; Soriente, Annunziata; Neri, Placido

doi:10.1016/j.tetasy.2005.05.039

Cited by 51 publications

(16 citation statements)

References 57 publications

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“…Calixarene 106,107 and crown ether 53,108-110 derivatives can be used as first coordination sphere ligands for placing two metal centres in an ideal position for cooperative activation of a substrate. Several phosphine-appended calixarene [111][112][113][114][115][116][117][118][119][120][121][122][123][124][125] and cyclodextrin [126][127][128][129][130][131][132] derivatives have been investigated as ligands in metal catalysis but only in a few cases the importance of the binding of the substrate within the cavity during the catalytic process has been demonstrated. 125,130 The same is true for other types of ligands or organocatalytic functions located at the upper part of calixarene or cyclodextrin backbones.…”

Section: Article Typementioning

confidence: 99%

Supramolecular catalysis. Part 2: artificial enzyme mimics

et al. 2014

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The design of artificial catalysts able to compete with the catalytic proficiency of enzymes is an intense subject of research. Non-covalent interactions are thought to be involved in several properties of enzymatic catalysis, notably (i) the confinement of the substrates and the active site within a catalytic pocket, (ii) the creation of a hydrophobic pocket in water, (iii) self-replication properties and (iv) allosteric properties. The origins of the enhanced rates and high catalytic selectivities associated with these properties are still a matter of debate. Stabilisation of the transition state and favourable conformations of the active site and the product(s) are probably part of the answer. We present here artificial catalysts and biomacromolecule hybrid catalysts which constitute good models towards the development of truly competitive artificial enzymes.

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Section: Article Typementioning

confidence: 99%

Supramolecular catalysis. Part 2: artificial enzyme mimics

et al. 2014

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“…The study of synthetic modeling systems for chiral recognition is an area of ever‐increasing research activity. Such model systems can find potential applications in the development of pharmaceuticals, enantioselective catalysis, separation, analysis of enantiomers, fundamental host–guest chemistry, and supramolecular material science . They can also contribute to better understanding of biological systems and their functions because chiral recognition is an essential phenomenon in living systems.…”

Section: Introductionmentioning

confidence: 99%

Syntheses and Highly Enantioselective Fluorescent Recognition of α‐Aminocarboxylic Acid Anions Using Chiral Oxacalix[2]arene[2]bisbinaphthes

Jiao

Yao

et al. 2012

Chirality

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The triazine-based bisbinaphthyl crown ethers oxacalix[2]arene[2]bisbinaphthes R-1, R-2, R-3 and S-1, S-2, S-3 were synthesized. The interactions of these compounds with various α-aminocarboxylic acid anions were studied. The crown ethers were found to carry out highly enantioselective fluorescent recognition of α-aminocarboxylic acid anions. It is observed that within a certain concentration range, one enantiomer of the chiral α-aminocarboxylic acid anions can increase the fluorescence intensity of the crown ethers by fivefold to sixfold, whereas the other enantiomer scarcely enhances the fluorescence. Such unusually high enantioselective responses make these crown ethers very attractive as fluorescent sensors in determining the enantiomeric composition of α-aminocarboxylic acid anions.

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“…Catalysis is another important application of calixarenes, and efficient catalytic systems based on calixarenes have been developed . However, calixarenes have seldomly been used for asymmetric catalysis . On the other hand, chiral ferrocenyl units are privileged ligands for asymmetric catalysis.…”

Section: Introductionmentioning

confidence: 99%

Chiral Phosphinoferrocenyl‐Calixarenes

et al. 2016

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The Mitsunobu alkylation of 4‐tert‐butylcalix[4]arene with (S)‐(2‐diphenylthiophosphinoferrocenyl)methanol followed by desulfuration of the thiophosphine unit using tris(dimethylamino)phosphine afforded enantiomerically pure calixarene mono‐ and di(ferrocenylphosphine) ligands in high yields. The calixarene mono(ferrocenylphosphine) ligands exhibited good catalytic activity but low atropoenantioselectivity when used in the asymmetric Suzuki–Miyaura coupling reaction of 1‐naphthaleneboronic acid and 1‐bromo‐2‐methylnaphthalene. However, the di(ferrocenylphosphine) ligand displayed both good catalytic activity and enantioselectivity (ee values up to 86 %) when employed in the asymmetric Tsuji–Trost allylic alkylation of 1,3‐diphenylprop‐2‐enyl acetate with dimethyl malonate.

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Synthesis of calix[4]arene derivatives bearing chiral pendant groups as ligands for enantioselective catalysis

Cited by 51 publications

References 57 publications

Supramolecular catalysis. Part 2: artificial enzyme mimics

Supramolecular catalysis. Part 2: artificial enzyme mimics

Syntheses and Highly Enantioselective Fluorescent Recognition of α‐Aminocarboxylic Acid Anions Using Chiral Oxacalix[2]arene[2]bisbinaphthes

Chiral Phosphinoferrocenyl‐Calixarenes

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