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Phosphine Organocatalysis

The hallmark of nucleophilic phosphine catalysis is the initial nucleophilic addition of a phosphine to an electrophilic starting material, producing a reactive zwitterionic intermediate, generally under mild conditions. In this Review, we classify nucleophilic phosphine catalysis reactions in terms of their electrophilic components. In the majority of cases, these electrophiles possess carbon-carbon multiple bonds: alkenes (section 2), allenes (section 3), alkynes (section 4), and Morita-Baylis-Hillman (MBH) alcohol derivatives (MBHADs; section 5). Within each of these sections, the reactions are compiled based on the nature of the second starting material – nucleophiles, dinucleophiles, electrophiles, and electrophile-nucleophiles. Nucleophilic phosphine catalysis reactions that occur via the initial addition to starting materials that do not possess carbon-carbon multiple bonds are collated in section 6. Although not catalytic in the phosphine, the formation of ylides through the nucleophilic addition of phosphines to carbon-carbon multiple bond-containing compounds is intimately related to the catalysis and is discussed in section 7. Finally, section 8 compiles miscellaneous topics, including annulations of the Hueisgen zwitterion, phosphine-mediated reductions, iminophosphorane organocatalysis, and catalytic variants of classical phosphine oxide-generating reactions.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H577NO – PubChem

 

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INHIBITORS OF PLASMA KALLIKREIN AND USES THEREOF

The present invention provides compounds and compositions thereof which are useful as inhibitors of plasma kallikrein and which exhibit desirable characteristics for the same.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H193NO – PubChem

 

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THERAPEUTIC INHIBITORY COMPOUNDS

The invention provides compounds of Formula I and Formula II: A-B-C-D-E-F-G-J (I) C-D-E-F-G-J (II) wherein A, B, C, D, E, F, G, and J have any of the values defined in the specification, and salts thereof. The compounds are useful for inhibiting plasma kallikrein, and for treating a disease or condition in an animal where inhibition of plasma kallikrein is indicated.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H166NO – PubChem

 

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Synthesis of Allenes by 1,6-Addition of Organocuprates to Acceptor-Substituted Enynes: Scope and Limitations

Acyclic acceptor-substituted conjugated enynes bearing sulfonyl, sulfinyl, sulfonate, nitro, amide, cyano, and oxazolidino groups at the double bond were synthesized and the regioselectivity of their reaction with organocuprates was examined.All Michael acceptors except enynes with nitro and amide functions underwent 1,6-additions, and the allenyl enolates thus formed were trapped with electrophiles in order to obtain the corresponding allenes.A qualitative reactivity scale for these reactions was established.The dependence of the regioselectivity of both the cuprate addition and the subsequent electrophilic capture on the acceptor group and the substitution pattern of the allenyl enolate were studied.Cyclic 2-en-4-ynoates with endocyclic double bonds were synthesized and treated with organocuprates to afford an exocyclic allene in one case. – Keywords: Allenes / 1,6-Addition / Cuprates, organo-/ Allenyl enolates / Electrophiles, regioselective reaction of

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Oxazolidine – Wikipedia,
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An entry to a chiral dihydropyrazole scaffold: Enantioselective [3 + 2] cycloaddition of nitrile imines

We have developed a versatile strategy to access dihydropyrazoles in highly enantioenriched form. Dipolar cycloaddition of electron-deficient acceptors and in situ-generated nitrile imines proceeds with high regio- and enantioselectivity using 10 mol % chiral Lewis acid catalyst. A variety of dihydropyrazoles that incorporate functionality for further manipulation have been prepared. Copyright

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Oxazolidine – Wikipedia,
Oxazolidine | C3H999NO – PubChem

 

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Ni@Pd nanoparticles supported on ionic liquid-functionalized KCC-1 as robust and recyclable nanocatalysts for cycloaddition of propargylic amines and CO2

Novel heterogeneous catalyst systems comprised of a fibrous nanosilica-supported nano-Ni@Pd-based ionic liquid (KCC-1/IL/Ni@Pd) are described for the cyclization of propargylic amines with CO2 to provide 2-oxazolidinones. KCC-1 with high surface area was functionalized with IL acting as a robust anchor so that the nano-Ni@Pd was well dispersed on the fibres of the KCC-1 microspheres, without aggregation. Because of the amplification effect of IL, high loading capacities of the nanocatalysts were achieved. The reported synthesis includes several advantages like solvent-free conditions, operational simplicity, short reaction times, environmentally benign reaction conditions, cost effectiveness, high atom economy and excellent yields, making it a genuinely green protocol.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H945NO – PubChem

 

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NOTE ON THE PREPARATION OF VERY ACTIVE N,N-BIS(2-OXO-3-OXAZOLIDINYL)-PHOSPHORODIAMIDIC CHLORIDE (Bop-Cl), AN EXTREMELY EFFECTIVE REAGENT FOR PEPTIDE FORMATION.

A preparation of high-quality coupling reagent Bop-Cl is reported.It fulfills the expectations of reproducibility in efficient peptide coupling reactions that are characterized by the formation of little side products and by clean work-up.

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BENZOFURAN AND BENZOTHIOPHENE DERIVATIVES USEFUL IN THE TREATMENT OF CANCERS OF THE CENTRAL NERVOUS SYSTEM

The present invention relates to benzofuran and benzothiophene derivatives and compositions containing such compounds for the production of medicaments for the treatment of cancers of the central nervous system as monotherapy or combination with other agents.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H246NO – PubChem

 

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Stereodivergent Synthesis of Trisubstituted Enamides: Direct Access to Both Pure Geometrical Isomers

A stereodivergent strategy has been developed to access either (E)- or (Z)-isomers of trisubstituted enamides. Starting from an extensive range of ketones, it was possible to synthesize and isolate the desired pure isomer by switching the reaction conditions. Lewis acid activation enables the formation of the (E)-isomers in high stereoselectivity (>90:10) and good yields. On the other hand, the use of a Br¡ãnsted acid allows the preparation of the (Z)-isomers, again in high selectivity (up to 99:1), with moderate yields.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H795NO – PubChem

 

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Preparation of N-alkoxycarbonyl-substituted cyclic lactams and ketones

N-alkoxycarbonyl-substituted cyclic lactams and nitrogen-containing cyclic ketones are prepared by reaction of a C1-20 alkyl ester of trichloroacetic acid with the corresponding cyclic lactam or nitrogen-containing cyclic ketone.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H201NO – PubChem