Recent Progress in Asymmetric Catalysis Using Chiral Carbohydrate‐Based Ligands

Diéguez, Montserrat; Claver, Carmen; Pàmies, Òscar

doi:10.1002/ejoc.200700082

Cited by 96 publications

(16 citation statements)

References 102 publications

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“…Recently, carbohydrates and their derivatives have emerged as an important tool for selective synthesis and as a chiral pool for the design of chiral ligands. They are used as chiral building blocks, precursors for drug synthesis and chiral catalysts in asymmetric catalysis (Dieguez et al, 2004a(Dieguez et al, , 2004b(Dieguez et al, , 2007Woodward et al, 2010;Boysen, 2007;Appelt et al, 2008). Despite the importance of carbohydrates in biological events, the pace of development of carbohydrate based therapeutics has been relatively slow.…”

Section: Resultsmentioning

confidence: 99%

Acylation of D-Glucose Derivatives over C5H5N: Spectral Characterization and in vitro Antibacterial Activities

Kawsar¹,

Uddin²,

Manchur³

et al. 2015

International J. of Biological Chemistry

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Methyl α-D-glucopyranoside was easily prepared by the treatment of D-glucose with anhydrous methyl alcohol in presence of hydrogen chloride at freezing temperature in good yield. Then N-acetylsulfanilylation of methyl α-D-glucopyranoside has been carried out by the direct method and afforded the 6-O-N-acetylsulfanilyl derivative in an excellent yield. In order to obtain newer products, the 6-O-N-acetylsulfanilyl derivative was further transformed to a series of 2,3,4-tri-O-acyl derivatives containing a wide variety of functionalities in a single molecular framework. The chemical structures of the newly synthesized compounds were elucidated by Fourier Transform Infrared spectroscopy (FTIR), 1 H-NMR (Proton nuclear magnetic resonance) spectroscopy elemental and physicochemical properties analysis. All the newly synthesized D-glucose derivatives were tested for their in vitro antibacterial activity against some human pathogenic bacterial strains. The study revealed that a good number of acylated products exhibited promising antibacterial activities. It is expected that the acylated derivatives of D-glucose may be considered as a potential source for developing new and better antibacterial agents against a number of pathogenic organism.

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Section: Resultsmentioning

confidence: 99%

Acylation of D-Glucose Derivatives over C5H5N: Spectral Characterization and in vitro Antibacterial Activities

Kawsar¹,

Uddin²,

Manchur³

et al. 2015

International J. of Biological Chemistry

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“…Two pyrene‐tagged diphosphite ligands were obtained following the procedure depicted in Scheme . First, the commercially available 1,2,5,6‐di‐isopropylideneglucofuranose ( 7 ) was treated with N‐bromosuccinimide and triphenylphosphine to provide the corresponding 6‐bromo derivative 8 followed by sodium nitrite treatment yielding the corresponding alcohol 9 ,. The alkylation of 9 was performed by reaction with either 1‐(bromomethyl)pyrene to afford 10 in 73 % yield, or with the freshly synthesised 4‐(pyren‐2‐yl)butyl trifluoromethanesulfonate affording 11 in 55 % yield.…”

Section: Resultsmentioning

confidence: 99%

“…These compounds were characterised by means of multinuclear NMR spectroscopy and MS. It is noteworthy that compared to the synthesis of the analogous ligand 4 a ,, no extra synthetic steps were required to prepare the pyrene tagged ligands 14 a and 15 a .…”

Section: Resultsmentioning

confidence: 99%

Highly Efficient Rh‐catalysts Immobilised by π‐π Stacking for the Asymmetric Hydroformylation of Norbornene under Continuous Flow Conditions

et al. 2019

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The application of C1‐symmetrical diphosphite ligands containing furanose backbone in the Rh‐catalysed asymmetric hydroformylation of norbornene is described. The catalysts were highly active and produced exclusively exo‐norbornanecarboxaldehyde with enantioselectivities (ee) up to 71 %. Considering these promising results, the ligands were modified with a pyrene moiety to accomplish their immobilisation onto carbon materials. The corresponding Rh complexes bearing the novel pyrene‐tagged ligands were synthesised and immobilised onto multiwalled carbon nanotubes (MWCNT), reduced graphene oxide (rGO) and carbon beads (CBs). The novel catalytic systems were tested in the asymmetric hydroformylation of norbornene providing similar performance in terms of both activity and selectivity compared to the non‐immobilised systems. The recyclability of the new heterogenised catalysts was studied in the target reaction in batch mode. Nevertheless, the recycling was unsuccessful due to catalyst leaching. When used under continuous flow mode, these catalysts revealed robust and provided even higher ee than the corresponding homogeneous systems.

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“…It is worth mentioning that carbohydrates and some basic amino acids are the most bio‐abundant groups of molecules that have environmentally benign natures and can provide promising cost benefits for industrial processes, and this is why they have high potential for use in various synthetic applications. Chemists are using these very often as the main precursors in the synthesis of natural compounds and pharmaceutically important drugs, while significant progress has been made in the field of selective catalytic reactions, where they have important roles as efficient bio‐based ligands …”

Section: Resultsmentioning

confidence: 99%

D‐Glucosamine in iron‐catalysed cross‐coupling reactions of Grignards with allylic and vinylic bromides: application to the synthesis of a key sitagliptin precursor

Sova

Frlan

Gobec

et al. 2015

Applied Organom Chemis

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A sustainable D-glucosamine ligand is successfully introduced into iron-catalysed C-C cross-coupling reactions for the first time. The Fe(acac) 2 /D-glucosamine·HCl/Et 3 N catalytic system was effective at 5 mol% loading in coupling reactions of Grignard reagents with organic bromides. Moderate to high efficiency was achieved with preserved stereochemistry when allyl (Csp 3 ) or alkenyl (Csp 2 ) bromides were coupled with phenylmagnesium (Csp 2 ) or benzylmagnesium (Csp 3 ) bromides. The catalytic system developed was also successfully applied for the novel and economic preparation of a Michael-acceptor-like starting material used in an alternative synthesis of the drug sitagliptin, a known blockbuster for the treatment of type II diabetes mellitus.

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Recent Progress in Asymmetric Catalysis Using Chiral Carbohydrate‐Based Ligands

Cited by 96 publications

References 102 publications

Acylation of D-Glucose Derivatives over C5H5N: Spectral Characterization and in vitro Antibacterial Activities

Acylation of D-Glucose Derivatives over C5H5N: Spectral Characterization and in vitro Antibacterial Activities

Highly Efficient Rh‐catalysts Immobilised by π‐π Stacking for the Asymmetric Hydroformylation of Norbornene under Continuous Flow Conditions

D‐Glucosamine in iron‐catalysed cross‐coupling reactions of Grignards with allylic and vinylic bromides: application to the synthesis of a key sitagliptin precursor

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