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Synthesis of new chiral auxiliaries for 6pi-azaelectrocyclization: 4- and 7-alkyl substituted cis-1-amino-2-indanols

The synthesis of new chiral auxiliaries, 7-alkyl substituted cis-1-amino-2-indanol derivatives, was established by the Diels-Alder reaction of 1-substituted dienes with cyclopentenone followed by the asymmetric epoxidation of the resulting indene derivatives and then the Ritter reaction. These bulky cis-aminoindanol derivatives are very effective as chiral auxiliaries and nitrogen sources in the asymmetric 6pi-azaelectrocyclization. The corresponding 4-alkyl derivative was also prepared using a similar method.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Two-carbon-elongated HIV-1 protease inhibitors with a tertiary-alcohol- containing transition-state mimic

A new generation of HIV-1 protease inhibitors encompassing a tertiary-alcohol-based transition-state mimic has been developed. By elongation of the core structure of recently reported inhibitors with two carbon atoms and by varying the P1? group of the compounds, efficient inhibitors were obtained with Ki down to 2.3 nM and EC50 down to 0.17 muM. Two inhibitor-enzyme X-ray structures are reported.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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METHODS TO TREAT ALZHEIMER’S DISEASE

The present invention is directed toward substituted hydroxyethylene compounds of formula (XII) useful in treating Alzheimer’s disease and other similar diseases.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The important role of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol

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Catalytic asymmetric bromochlorination of aromatic allylic alcohols promoted by multifunctional Schiff base ligands

It was found that the tridentate O,N,O-type Schiff base ligand bearing suitable substituents was a highly effective promoter in the catalytic asymmetric bromochlorination reaction, in which the corresponding aromatic bromochloroalcohols with vicinal halogen-bearing stereocenters were formed with perfect regioselectivity, with moderate to excellent enantioselectivities (up to 93% ee), and with good yields and chemoselectivities.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Planar chiral ferrocene salen-type ligands featuring additional central and axial chirality

We report on novel chiral tridentate [NO2]H2 and tetradentate [N2O2]H2 Schiff base ligands containing a planar chiral ferrocene moiety linked to hydroxyl-imine or diimine donors with central or axial chirality. Structurally, these ligands resemble half-salen and salen systems designed for stereoselective applications of their transition metal complexes in homogeneous catalysis. The modular synthesis involves diastereoselective metalation of chiral ferrocene or pentamethylferrocene acetals, followed by stereoconservative hydroxyalkylation and condensation with chiral hydroxyamines or diamines, respectively. In comparison to salen-type systems, an important advantage of these ligands is their tunable steric protection of the alkoxide donor site. A total of 18 different ligands varying in electronic and steric properties have been prepared and fully characterized by NMR, IR, mass spectroscopy and by single crystal structure analysis of nine precursors and representatives.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Brief introduction of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol

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Synthesis of new chiral calix[4]arene thiourea derivatives for enantiomeric recognition of carboxylate anions

The study of enantiomeric recognition of amino acid and carboxylic acid compounds is of significance since these compounds are basic building blocks of biological molecules. Enantiomeric recognition and separation of these compounds are among the main topics of supramolecular chemistry since they are basic building blocks of biological molecules and a number of them are known to possess potent biological activities. In this study the synthesis of novel chiral calix[4]arene thiourea derivatives has been reported. The enantioselectivity of chiral receptors was investigated by using UV-Vis spectroscopy. All the chiral calix[4]arene derivatives exhibited certain chiral recognition towards the enantiomers of alpha-hydroxy isovaleric acid (HIVA), mandelic acid (MA), 2-chloromandelic acid (2-ClMA) and N-Boc-alanine (NBocAl). The receptors with hydrogen bonding sites and aromatic groups showed considerable higher stereoselectivities. As a chiral receptor, calix[4]arene 2-hydroxy-1,2 diphenyl ether thiourea derivative has enantiomeric discriminating ability for 2-chloromandelic acid (up to KR/ KS = 2.80) at 25 C. The enantiomeric recognition abilities for guests are also discussed from a thermodynamic point of view.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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An efficient synthesis of indane-derived bis(oxazoline) and its application to hetero Diels-Alder reactions on polymer support

Indane-derived bis(oxazolines) were synthesized in two steps and 93% overall yield starting from commercially available substrates. This ligand is as effective as tert-butyl bis(oxazoline) in hetero Diels-Alder reaction both in solution and on polymer support.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Lipase-mediated resolution of inden-1-ol

Optically pure inden-1-ol has been obtained efficiently in both enantiomeric forms via kinetic deacylation of racemic 1-acetoxyindene using lipase PS.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Synthesis and biological evaluation of novel homochiral carbocyclic nucleosides from 1-amino-2-indanols

New chiral purinyl and 8-azapurinyl carbanucleoside derivatives based on indanol were synthesized from commercial available (1S,2S)-trans-1-amino-2- indanol and (1R,2R)-trans-1-amino-2-indanol using a linear methodology. The antiviral activity and cytotoxicity of these compounds were evaluated against herpes simplex virus type 1 (HSV-1) in Vero cells, bovine viral diarrhea virus (BVDV) in Mardin-Darby bovine kidney (MDBK) cells and hepatitis B virus (HBV) in HepG2 2.2.15 cell line. Three compounds, showed an inhibition of the HBsAg levels similar to reference drug lamivudine. One chloropurinyl nucleoside, derived from the cis-1-amino-2-indanol, was cytotoxic on MDBK cells and it could be a lead for developing anticancer agents.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

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Highly diastereoselective dielsalder reaction mediated by a chiral auxiliary derived from amino indanol: The role of conformation on diastereoselectivity

The oxazolidinone 2 derived from amino indanol 1 functions as a very efficient chiral auxiliary for the Diels-Alder reaction. The effect of conformation has been explored using a range of constrained phenyl glycinol analogues.

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Reference£º
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis