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Asymmetric access to peptidyl beta3-aldehydes by coupling of N-phthalyl alpha-amino acids with a synthetic heterocyclic beta-amino aldehyde precursor

Asymmetric access to novel N-protected (di)peptidyl beta3- aldehydes (“beta3-PAs”) has been achieved through direct coupling of a chiral non-racemic 6-alkoxytetrahydrooxazinone with N-phthalyl L-alpha-amino acids. Kinetic resolution allows for the fruitful use of racemic amino acids in this process. Acidic hydrolysis of the diastereomerically pure, coupling products leads to the title N-phthalyl-beta3-PAs in high yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1178NO – PubChem

 

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Cu-catalyzed oxidative amidation of propiolic acids under air via decarboxylative coupling

Figure presented A Cu-catalyzed aerobic oxidative amidation of propiolic acids via decarboxylation under air has been developed. Only carbon dioxide is produced as byproduct in this approach. The use of air as oxidant makes this method more useful and easy to handle.

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Oxidative amidation of activated alkenes using Pd(OAc)2 as a catalyst precursor

A new “chloride-free” protocol was developed for oxidative amidation reactions between cyclic and acyclic amides and carbamates with activated olefins, conducted under Pd/Cu catalysis, using air as a terminal oxidant. The presence of TsOH is important for catalytic activity. The scope of the reaction includes the addition of primary amides, carbamates, as well as cyclic oxazolidinone and pyrrolidinone. The reactions are found to be sensitive to steric demand of the N-nucleophile, and E-selectivity can be achieved exclusively with cyclic N-nucleophiles. The products can be easily hydrogenated to afford the saturated product in high yields.

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Proteasome inhibitors: Dozens of molecules and still counting

The discovery of the proteasome in the late 80’s as the core protease of what will be then called the ubiquitin-proteasome system, rapidly followed by the development of specific inhibitors of this enzyme, opened up a new era in biology in the 90’s. Indeed, the first proteasome inhibitors were instrumental for understanding that the proteasome is a key actor in most, if not all, cellular processes. The recognition of the central role of this complex in intracellular proteolysis in turn fuelled an intense quest for novel compounds with both increased selectivity towards the proteasome and better bioavailability that could be used in fundamental research or in the clinic. To date, a plethora of molecules that target the proteasome have been identified or designed. The success of the proteasome inhibitor bortezomib (Velcade) as a new drug for the treatment of Multiple Myeloma, and the ongoing clinical trials to evaluate the effect of several other proteasome inhibitors in various human pathologies, illustrate the interest for human health of these compounds.

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Oxazolidine – Wikipedia,
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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,
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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,
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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,
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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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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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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,
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