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Heterocycles with a Stereogenic Phosphorus or Sulfur Atom Derived from Aminoalcohols or Aminonaphthols

This chapter presents the synthesis of heterocycles with a stereogenic phosphorus or sulfur atom derived from aminoalcohols or aminonaphthols, which has been reported recently (usually after 2002). It also contains selected references to the earlier papers and is divided into three sections, describing methods of synthesis of the three particular classes of heterocyclic derivatives. The first two are devoted to heterocycles with a stereogenic phosphorus atom and discuss the protocols for the preparation of 1,3,2-oxazaphospholanes (1,3,2-oxazaphospholidines) with a tri- and tetracoordinated phosphorus atom, 1,3,2-oxazaphosphorinanes and larger rings containing a stereogenic phosphorus atom forming part of the nitrogen-phosphorus-oxygen (NPO) grouping. The third section concerning heterocycles with a stereogenic sulfur atom describes the synthesis of all kinds of 1,2,3-oxathiazolidine 2-oxides and tetrahydro-1,2,3-oxathiazine-2-oxides.

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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

Extended knowledge of C9H11NO

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Optically pure 1-amido-2-indanols

A two-step process for the conversion of a trans-1-amino-2-hydroxycycloalkane stereoselectively to a cis-1-amino-2-hydroxycycloalkane is disclosed. The novel step, a one-step hydrolysis with formal inversion, can be used to convert an amide of a trans-1-amino-2-hydroxycycloalkane to a cis-1-amino-2-hydroxycycloalkane. Methods for obtaining the trans-1-amino-2-hydroxycycloalkanes and their amides from alkenes are also disclosed. Novel, optically active 1-amido-2-indanols and 1-amino-2-alkanols 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

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

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Enhanced efficiency of thiourea catalysts by external Bronsted acids in the Friedel-Crafts alkylation of indoles

A novel study on the influence of external Bronsted acids on thiourea catalysts in the asymmetric Friedel-Crafts alkylation of indoles with nitroalkenes is reported. The final 3-substituted indole derivatives were synthesized with better results because of cooperative effects between the chiral thiourea and a Bronsted acid additive (1a·HA). The effects of diverse catalysts, different acid additives, solvents, and temperatures in the reaction were also explored. The high reactivity and selectivity of the reaction is presumptively attributed to an appropriate assembly between the Bronsted acid and the thiourea structure, affording a more acidic and rigid catalytic complex. Copyright

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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 homogeneous catalysis, catalysts are in the same phase as the reactants. Chemistry is traditionally divided into organic and inorganic chemistry. Safety of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol, Catalysts allow a reaction to proceed via a pathway that has a lower activation energy than the uncatalyzed reaction. In an article,Which mentioned a new discovery about 126456-43-7

HIV-1 protease inhibitors with picomolar potency against PI-resistant HIV-1 by modification of the P1? substituent

Transposition of the pyridyl nitrogen from the P3 substituent to the P1? substituent in HIV-1 protease inhibitors (PI) affords compounds such as 3 with an improved inhibitory profile against multiple P450 isoforms. These compounds also displayed increased potency, with 3 inhibiting viral spread (CIC95) at <8 nM for every strain of PI-resistant HIV-1 tested. The poor to modest bioavailability of these compounds may correlate in part to their aqueous solubility. The design and synthesis of related molecules that are more effective, more selective, and less toxic than aspirin are important objectives of biomedical research.Safety of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol, If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 126456-43-7, in my other articles.

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

Archives for Chemistry Experiments of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol

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Process for preparing an optically active phenylglycidyl acid derivative

The invention relates to a process for preparing an optically active trans-compound having formula (1), in which R represents a phenyl group, whether or not substituted, preferably p-methoxyphenyl, and A is derived from an optically active compound, in which an aldehyde having formula (2), in which R is as defined above, is, in the presence of a base, brought into contact with an optically active acetyl compound having formula (3), in which X represents a leaving group and in which A is derived from an amino alcohol, preferably a beta-amino alcohol having a rigid structure.Particularly good results were obtained when use was made of a compound having formula (3), in which A is derived from an amino indanol compound having formula (4), in which R 1 and R 2 represent a (hetero)alkyl or (hetero)aryl group, whether or not substituted, having 1-10 C atoms, or R 1 and R 2 constitute an aromatic or aliphatic ring together with the N atom to which they are bound, in particular in which R 1 and R 2 each independently of one another represent methyl, ethyl, isopropyl, n-propyl, n-butyl, allyl, benzyl or tosyl.

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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

Final Thoughts on Chemistry for (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol

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Design and synthesis of HIV-1 protease inhibitors. Novel tetrahydrofuran P2/P2?-groups interacting with Asp29/30 of the HIV-1 protease. Determination of binding from X-ray crystal structure of inhibitor protease complex

A series of HIV-1 protease inhibitors having new tetrahydrofuran P2/P2? groups have been synthesised and tested for protease inhibition and antiviral activity. Six novel 4-aminotetrahydrofuran derivatives were prepared starting from commercially available isopropylidene-alpha-D-xylofuranose yielding six symmetrical and six unsymmetrical inhibitors. Promising sub nanomolar HIV-1 protease inhibitory activities were obtained. The X-ray crystal structure of the most potent inhibitor (23, Ki 0.25 nM) co-crystallised with HIV-1 protease is discussed and the binding compared with inhibitors 1a and 1b.

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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 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:
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

Archives for Chemistry Experiments of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol

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Lipase-mediated kinetic resolution of cis-1,2-indandiol and the Ritter reaction of its mono-acetate

Lipase-mediated kinetic resolution of cis-1,2-indandiol 5 in the presence of lipase PS was examined. Enantiomerically enriched (1S,2R)-2-acetoxy-1-indanol 6a was obtained when cis-1,2-indandiol 5 was treated with one equivalent of vinyl acetate. Treatment of 5 with two equivalents of vinyl acetate furnished a mixture of (1R,2S)-2-acetoxy-1-indanol 6a and (1R,2S)-1-acetoxy-2-indanol 6b. A route to both enantiomers of 1 was also developed by using the enantiomerically enriched mono-acetate thus obtained.

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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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Heterocyclic Compound

The present invention provides a compound represented by the formula wherein each symbol is as defined in the specification, or a salt thereof. The compound of the present invention shows a strong IAP antagonistic activity.

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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

Extended knowledge of C9H11NO

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Enantioselective Aza-Henry reaction with an N-sulfinyl urea organocatalyst

A new class of organocatalyst has been developed that incorporates a sulfinyl group as a urea or thiourea substituent. The sulfinyl group serves to simultaneously acidify the urea and provide asymmetric induction in hydrogen-bond-catalyzed reactions. The utility of this new catalyst structure is demonstrated by the high selectivity provided in the aza-Henry reaction not only for aromatic N-Boc imine substrates but also for aliphatic imines for which enantioselective H-bonding catalysis has not previously been demonstrated. Copyright

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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