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Iridium catalysts for the asymmetric hydrogenation of olefins with nontraditional functional substituents

Chiral iridium catalysts have now been used in the asymmetric hydrogenation of largely unfunctionalized olefins for a decade. Recently, they have also been applied to substrates with more exotic functional groups, including non-coordinating ones. These, unlike coordinating substituents, cannot direct asymmetric hydrogenation by rhodium- or ruthenium-based catalysts. This review discusses several classes of these less familiar substrates, outlines the progress that has been made toward their stereoselective hydrogenation, and highlights the role of iridium complexes in this emerging field. We hope this will inspire researchers to consider iridium-catalyzed asymmetric hydrogenation as a potential route to a broad range of chiral compounds.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H443NO – PubChem

 

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Preparation of 2-aminoalkanesulfonic acid

The invention is a process for the preparation of the metal salt of 2-aminoalkanesulfonic acid which comprises contacting a 2-oxazolidinone with a water-soluble metal sulfite or a water-soluble metal hydrogen sulfite in aqueous solution under conditions such that a metal salt of 2-aminoethanesulfonic acid is prepared.

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Oxazolidine – Wikipedia,
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Photo-oxidation of Oxazolidones and Hydantoins in the Presence of Benzophenone

Irradiation in the presence of benzophenone and oxygen of nitrogen-containing heterocycles having an NCO group yields products arising out of regioselective oxidation alpha to the nitrogen atom.Direct irradiation (in the absence of benzophenone and oxygen) of 5-methyl- and 5,5-dimethyl-hydantoins yields allophanates.The first step of this reaction involves the homolysis of the C(4) – C(5) bond of the hydantoin.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H568NO – PubChem

 

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Regioselective Hydroamination Using a Directed Nucleopalladation/Protodepalladation Strategy

Alkene hydroamination is an attractive approach for converting alkenes into structurally complex amine products. Several different strategies have been pursued over the past few decades to achieve this historically challenging reaction. One of the key issues associated with this transformation is control of regioselectivity, which is particularly difficult for internal non-conjugated alkenes. Our group has recently found success using a removable bidentate auxiliary to control regioselectivity and stabilize the key nucleopalladated intermediate in a palladium(II)-catalyzed alkene hydroamination with N-H nucleophiles. This article describes the historical context for this work, the underlying conceptual logic, our results to date, and the future outlook.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H579NO – PubChem

 

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Tandem chain extension-Mannich reaction: An approach to beta-proline derivatives

A zinc carbenoid-initiated chain extension reaction provides access to an organometallic intermediate, which can be used to capture activated imines. Deprotection of the nitrogen and reduction provides access to racemic derivatives of beta-proline. The relative stereochemistry of the beta-proline can be controlled through use of different activating groups on the imine nitrogen.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H652NO – PubChem

 

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COMPOUNDS AND THEIR METHODS OF USE

The present invention is directed to, in part, fused heteroaryl compounds and compositions useful for preventing and/or treating a disease or condition relating to aberrant function of a voltage-gated, sodium ion channel, for example, abnormal late/persistent sodium current. Methods of treating a disease or condition relating to aberrant function of a sodium ion channel including Dravet syndrome or epilepsy are also provided herein.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H209NO – PubChem

 

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Sulfonyl bis-N-oxazolidinone (SBO): A new versatile dielectrophile with sequential reactivity

The sulfonylbis-N-oxazolidinone (SBO) was designed as a biscarbamoylating reagent Its synthesis was easily carried out starting from sulfuryl chloride, chlorosulfonyl isocyanate or sulfonylbis-isocyanate, using oxazolidinone and/or 2 -haloethanol in one-pot procedures. The structure of SBO was established by X-ray crystallography. The difference of reactivity of both electrophilic carbonyl centers allows the formation of dissymetric linkages.

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Oxazolidine – Wikipedia,
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A novel 1beta-methylcarbapenem antibiotic, S-4661 synthesis and structure-activity relationships of 2-(5-substituted pyrrolidin-3-ylthio)-1beta-methylcarbapenems

The synthesis and biological activity of (1R,5S,6S)-2-[(3S,5S)-5-substituted pyrrolidin-3-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acids are described. These compounds exhibit potent antibacterial activity against a wide range of both Gram-positive and Gram-negative bacteria including Pseudomonas aeruginosa. Of these new carbapenems, (1R,5S,6S)-2-[(3S,5S)-5-sulfamoylaminomethyl pyrrolidin-3-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid (S-4661) showed the most potent and well balanced activity and was selected as a candidate for further evaluation.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H648NO – PubChem

 

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CuO nanoparticles catalyzed C-N, C-O, and C-S cross-coupling reactions: Scope and mechanism

CuO nanoparticles have been studied for C-N, C-O, and C-S bond formations via cross-coupling reactions of nitrogen, oxygen, and sulfur nucleophiles with aryl halides. Amides, amines, imidazoles, phenols, alcohols and thiols undergo reactions with aryl iodides in the presence of a base such as KOH, Cs 2CO3, and K2CO3 at moderate temperature. The procedure is simple, general, ligand-free, and efficient to afford the cross-coupled products in high yield.

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Oxazolidine – Wikipedia,
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The biological effects of structural variation at the meta position of the aromatic rings and at the end of the alkenyl chain in the alkenyldiarylmethane series of non-nucleoside reverse transcriptase inhibitors

In an effort to elucidate a set of structure-activity relationships in the alkenyldiarylmethane (ADAM) series of non-nucleoside reverse transcriptase inhibitors, a number of modifications were made at two locations: (1) the meta positions of the two aromatic rings and (2) the end of the alkenyl chain. Forty-two new ADAMs were synthesized and evaluated for inhibition of the cytopathic effect of HIV-1RF in CEM-SS cell culture and for inhibition of HIV-1 reverse transcriptase. The size of the aromatic substituents was found to affect anti-HIV activity, with optimal activity appearing with Cl, CH3, and Br substituents and with diminished activity occurring with smaller (H and F) or larger (I and CF3) substituents. The substituents at the end of the alkenyl chain were also found to influence the antiviral activity, with maximal activity associated with methyl or ethyl ester groups and with diminished activity resulting from substitution with higher esters, amides, sulfides, sulfoxides, sulfones, thioesters, acetals, ketones, carbamates, ureas, and thioureas. Twelve of the new ADAMs displayed submicromolar EC50 values for inhibition of the cytopathic effect of HIV-1RF in CEM-SS cells. Selected ADAMs, 19 and 21, were compared to previously published ADAMs 15 and 17 for antiviral efficacy and activity against the HIV-1 reverse transcriptase enzyme. All four ADAMs were found to inhibit HIV-1 reverse transcriptase enzyme activity, to inhibit the replication of a variety of HIV-1 clinical isolates representing syncytium-inducing, nonsyncytium-inducing, and subtype representative isolates, and to inhibit HIV-1 replication in monocytes. Subsequent assessment against a panel of site-directed reverse transcriptase mutants in NL4-3 demonstrated no effect of the K103N mutation on antiviral efficacy and a slight enhancement (6- to 11-fold) in sensitivity to AZT-resistant viruses. Additionally, ADAMs 19 (44-fold) and 21 (29-fold) were more effective against the A98G mutation (found in association with nevirapine resistance in vitro), and ADAM 21 was 5-fold and 2-fold more potent against the Y181C inactivation mutation than the previously reported ADAMs 15 and 17, respectively. All four ADAMs were tested for efficacy against a multidrug-resistant virus derived from a highly experienced patient expressing resistance to the reverse transcriptase enzyme inhibitors AZT, ddI, 3TC, d4T, foscarnet, and nevirapine, as well as the protease inhibitors indinavir, saquinavir, and nelfinavir. ADAM 21 was 2-fold more potent than ADAM 15 and 6-fold more potent than ADAMs 17 and 19 at preventing virus replication. Thus, we have identified a novel series of reverse transcriptase inhibitors with a favorable profile of antiviral activity against the primary mutation involved in clinical failure of non-nucleoside reverse transcriptase inhibitors, K103N, and that retain activity against a multidrug-resistant virus.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H1156NO – PubChem