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Different L-prolinamides 21, prepared from L-proline and chiral beta-amino alcohols are active bifunctional catalysts for the direct nitro-Michael addition of ketones to beta-nitrostyrenes. In particular, catalyst 21e, prepared from L-proline and (1S,2R?)-cis-1-amino-2-indanol, exhibits the highest catalytic performance working in polar aprotic solvents such as NMP, especially in the presence of 20 mol-% of acid additives such as p-nitrobenzoic acid or under microwave heating. High syn diastereoselectivities (up to 94 % de) and good enantioselectivities (up to 80 % ee) are obtained at room temp. Moreover, catalyst 21e can be easily recovered and reused. ESI-MS studies are used to characterize the intermediates assumed for the catalytic cycle. The stereochemical control attending Michael addition reactions between ketones and nitrostyrenes catalyzed by prolinamide derivatives 21 has been investigated with computational density functional methods. Transition-state energies for the rate-limiting C-C bond-forming step are calculated. Analysis of these structures indicates that hydrogen bonding plays an important role in catalysis, and that the energy barrier for Re-face attack to form syn-(4S,5R) products is lower than that for Si-face attack leading to syn-(4R,5S) products. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

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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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A H2O-regulated chemoselective addition in oxa- and aza-Michael reactions for aminoalcohols and mixtures of structurally similar alcohols and amines was reported. The oxa-Michael reactions might be kinetically controlled, and the reactions to produce O-selective products were slowed by the addition of water. The electrophilicity of Michael acceptors and the steric hindrance of Michael donors also affect the ratios of O/N products. This method offers novel ideas over conventional metal-catalyzed or ligand-induced strategies.

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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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A diastereomeric mixture of the alpha-amino nitrile prepared by the Strecker reaction of benzaldehyde, (1S,2R)-1-aminoindan-2-ol, and cyanotrimethylsilane thermally epimerizes in the solid state to give a single diastereomer with an (S)-configuration at the alpha position to the nitrile moiety. This shows a sharp contrast to the reaction conducted in DMSO at room temperature, which gives a 1:1 mixture of (S)- and (R)-isomers. Several other alpha-amino nitriles also epimerize in the solid-state toward single diastereomers.

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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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A method for the enantioselective reduction of prochiral ketones using catalytic amounts of tetrahydroindeno[1,2-d][1,3,2] oxazaboroles of formula II is disclosed. STR1 The oxazaboroles can be generated in situ from the corresponding cis-1-amino-2-indanols or imino indanols (III) STR2 Novel compounds of formulas II and III are also disclosed.

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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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A process for making a clinically efficacious HIV protease inhibitor Compound J eliminates one step in its synthesis, by an improved, alternative synthesis of the 2(S)-4-picolyl-2-piperazine-t-butyl-carboxamide intermediate.

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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. Computed Properties of C9H11NO, Name is (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol, belongs to chiral-nitrogen-ligands compound, is a common compound. Computed Properties of C9H11NOCatalysts allow a reaction to proceed via a pathway that has a lower activation energy than the uncatalyzed reaction. In an article, authors is , once mentioned the new application about Computed Properties of C9H11NO.

Compounds of the formula (I): Wherein R1, R2, X and N are as defined in the specification; E is N, CH; A1 and A” are terminal groups as defined in the specification. The compounds have utility as HIV-I protease inhibitors. ”

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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. SDS of cas: 126456-43-7, Name is (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol, belongs to chiral-nitrogen-ligands compound, is a common compound. SDS of cas: 126456-43-7Catalysts allow a reaction to proceed via a pathway that has a lower activation energy than the uncatalyzed reaction. In an article, authors is , once mentioned the new application about SDS of cas: 126456-43-7.

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:
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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An expeditious synthetic approach to chiral phenol 1, a key building block in the preparation of a series of drug candidates, is reported. The strategy includes a cost-effective and readily scalable route to cyclopentanone 3 from isobutyronitrile (10). The sterically hindered and enolizable ketone 3 was subsequently employed in a challenging Grignard addition mediated by LaCl 3?2LiCl. A novel preparation of the lanthanide reagent required for this transformation is described. To complete the process, a highly enantioselective hydrogenation step afforded the target (1). The importance of the phenol group to the success of this asymmetric transformation is discussed.

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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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Herein, we report the first example of the asymmetric hydrogenation of a prochiral benzodiazepine substrate as key transformation in a pilot-scale synthesis of BET inhibitor BAY 1238097. High-throughput screening in a parallel reactor enabled us to identify an efficient catalyst based on Ir and a chiral bisphosphine. An additive screening allowed significant reduction of catalyst loading. Ultimately, the hydrogenation was performed on a kilogram scale leading to the production of 27 kg of the desired product with an enantiomeric excess of 99% after 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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The enantiomeric excess is a key parameter for chemical and pharmaceutical industries for its ability to determine the activity and therapeutic action of chiral compounds. The determination of the enantiomeric excess using nuclear magnetic resonance is generally based on the formation of diastereomeric complexes. Herein we report novel chiral oxo-bridged calix[2]arene[2]triazine derivatives, which were synthesized from (1S,2R)-(-)-1-amino-2-indanol or (1S,2R)-(+)-2-amino-1,2-diphenylethanol. The structures of these compounds were established by various spectroscopic methods. Their enantiomeric recognition abilities towards the enantiomers of alpha-racemic carboxylic acids were examined by using 1H NMR spectroscopy. The DeltaDeltadelta values of alpha-H signals were appropriate to give a good baseline resolution for most of the tested analytes, which ranged from 0.005 to 0.053 ppm. The alpha-hydroxy acids, especially those containing aromatic group such as mandelic acid, alpha-methoxyphenylacetic acid, showed a bigger DeltaDeltadelta value in comparison to the other carboxylic acids.

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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