Properties and Exciting Facts About (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol

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Mechanistic aspects of the stereospecific interaction for aminoindanol with a crown ether column

Investigations into the mechanistic aspects of the stereospecific interaction of the four optical isomers of aminoindanol on a silica based crown ether column were performed. The nature and concentration of the mobile phase’s counteranion affected the hydrophobic interaction but had little effect on the inclusion interaction. Minimal changes in the separation factor of the enantiomers were observed in the pH range of 1-5.2, but a minimum in the capacity factor was observed at pH 3.75. Van’t Hoff plots indicated a high entropy and a positive enthalpy at pH 5.2, while a lower entropy and a negative enthalpy were observed at and below pH 3.75. Hill plots indicated that there were more active binding sites at pH 3.0 as compared to pH 1.0 and that the binding ratio of aminoindanol to active sites was also greater. Apparently at higher pH values, as the silica becomes deprotonated, there is an additional electrostatic interaction between the protonated aminoindanol and the deprotonated silica sites.

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

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Catalytic chemoselective conjugate addition of amino alcohols to alpha,beta-unsaturated ester: Hydroxy group over amino group and conjugate addition over transesterification

A highly chemoselective conjugate addition of amino alcohols to alpha,beta-unsaturated ester using a soft Lewis acid/hard Br°nsted base cooperative catalyst was developed. This catalysis achieved chemoselective addition of a hydroxy group over an amino group. Moreover, soft metal alkoxide generation enabled chemoselective soft conjugate addition over hard transesterification. Various amino alcohols, including unprecedented cyclic beta-amino alcohol, were applicable to the present catalysis.

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

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Computational (MM, MD and MDMM) study of bidentate complexes of (R,R)- and meso-alpha,alpha?-bis(trifluoromethyl)-9,10-anthracenedimethanol with cis-1-amino-2-indanol

Results are reported from molecular mechanics (MM), molecular dynamics (MD) and a combined mode – MD with a subsequent MM minimization, of the complexes of the chiral solvating agent (CSA) alpha,alpha?-bis(trifluoromethyl)-9,10-anthracenedimethanol (1) in two of its diastereoisomeric forms ((R,R)- and meso-) with the substrates (1S,2R)- and (1R,2S)-cis-1-amino-2-indanol (2). Our computational work was stimulated by preceding NMR study of the enantio differentiation capacity of the CSA manifested in the formation of bidentate complexes with the substrates. The molecular modeling and simulation studies gave possible structures and relative stabilities of the associated species. MM minimizations were sufficient in order to find the lowest energy minima of meso-1/(1S,2R)-2 and (R,R)-1/(1S,2R)-2, while the lowest energy structure of (R,R)-1/(1R,2S)-2 was detected after the MD and MDMM studies. The complexes with the (R,R)-1 isomer have higher total energies than those with meso-1, in accord with an NMR estimate for longer lifetimes of the complexes with meso-1.

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

Properties and Exciting Facts About C9H11NO

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Enantioselective alpha-hydroxylation of -ketoamides

The first enantioselective alpha-hydroxylation reaction of alpha-substituted -ketoamides has been developed by using the commercially available hydroquinine/TBHP system. The tertiary alcohols are obtained in good to high yield and up to 83% ee, which can be improved by a single crystallization.

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

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Enantioselective preparation and structural and conformational analysis of the chiral solvating agent alpha,alpha?-bis(trifluoromethyl)-1,8- anthracenedimethanol

The preparation of the enantiomers of alpha,alpha?- bis(trifluoromethyl)-1,8-anthracenedimethanol is described, and their conformational behaviour studied. These enantiomers are very active when used as chiral solvating agents in the presence of several compounds.

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

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Multifunctional isoquinoline-oxazoline ligands of chemical and biological importance

Multifunctional isoquinoline-oxazolines (MIQOXs) were conceived and synthesized from commercially available chiral amino acids. The multifunctional role of MIQOXs was demonstrated by Pd-catalyzed highly enantioselective addition of arylboronic acids to nitrostyrenes, and by the discovery of novel antifungal candidates.

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

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In heterogeneous catalysis, catalysts provide a surface to which reactants bind in a process of adsorption. Safety of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol, Name is (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol, belongs to chiral-nitrogen-ligands compound, is a common compound. Safety of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-olCatalysts allow a reaction to proceed via a pathway that has a lower activation energy than the uncatalyzed reaction. In an article, authors is Herrera, Raquel P., once mentioned the new application about Safety of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol.

Organocatalytic conjugate addition of formaldehyde N,N-dialkylhydrazones to beta,gamma-unsaturated alpha-keto esters

(1S,2R)-1-Aminoindan-2-ol-derived thioureas behave as efficient H-bonding organocatalysts for the nucleophilic conjugate addition of formaldehyde hydrazones to beta,gamma-unsaturated alpha-keto esters as enoate surrogates, affording the corresponding adducts in good yields and enantioselectivities.

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

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General and Stereoselective Method for the Synthesis of Sterically Congested and Structurally Diverse P-Stereogenic Secondary Phosphine Oxides

A general and efficient method for the synthesis of bulky and structurally diverse P-stereogenic chiral secondary phosphine oxides (SPOs) by using readily available chiral amino alcohol templates is described. These chiral SPOs could be used as chiral building blocks for the synthesis of difficult-to-access bulky P-stereogenic phosphine compounds or ligands for organic catalysis.

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

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Discovery of potent HIV-1 protease inhibitors incorporating sulfoximine functionality

Based on the unique property of sulfoximine and the homodimeric C2 structural symmetry of HIV-1 protease, a novel class of sulfoximine-based pseudosymmetric HIV-1 protease inhibitors was designed and synthesized. The sulfoximine moiety was demonstrated to be important for HIV-1 protease inhibitor potency. The most active stereoisomer (2S,2?S) displays a potency of 2.5 nM (IC50) against HIV-1 protease and an anti-HIV-1 activity of 408 nM (IC50). A possible mode of action is proposed.

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

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Development of bifunctional aza-bis(oxazoline) copper catalysts for enantioselective henry reaction

Base-functionalized aza-bis(oxazoline) ligands were prepared to explore the concept of dual activation through the Lewis acid and a tethered tertiary amine base. The catalytic activity of the Cu complex was evaluated for the asymmetric Henry reaction. Compared with a corresponding unfunctionalized copper complex with external 1-benzyl-4-ethylpiperazine base, the ethylpiperazine- functionalized aza-bis(oxazoline) copper catalyst resulted in rate acceleration (2.5 times) as well as improved enantioselectivity (72% ee vs 92% ee).

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