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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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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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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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Discovery of Oxazolidin-2-one

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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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Extracurricular laboratory:new discovery of 5,5-Dimethyloxazolidine-2,4-dione

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Alterations in mouse embryo intracellular pH by DMO during culture impair implantation and fetal growth

The preimplantation embryo is highly susceptible to in-vitro stress, and although this does not necessarily perturb blastocyst development, it can significantly affect embryo physiology and the ability to form a viable pregnancy. This study determined that the preimplantation mouse embryo is highly sensitive to a small decrease in intracellular pH (<0.2 pH units). Embryos cultured in media containing a weak acid (5,5-dimethyl-2,4-oxazolidinedione; DMO) formed blastocysts with decreased cell number and inner cell mass number, as well as increased apoptosis, even though blastocyst development and morphology were unchanged. Interestingly, the effects were similar regardless of whether the pH stress was present for a short-term 'acute' exposure (during the zygote to 2-cell, or 2-cell to 8-cell division) or an extended 'chronic' period of time (continually from the zygote to the blastocyst stage). Exposure to DMO during the first cleavage division did not alter implantation; however, fetal weight and crown-rump length were significantly decreased (P < 0.05). In contrast, continuous exposure to DMO throughout preimplantation development reduced not only implantation but also fetal weight and crown-rump length. This study highlights the importance of correct intracellular pH and demonstrates that slight deviations can significantly impact embryo development and viability. The early embryo is known to be sensitive to its environment. This study determined the effect of a small alteration to pH of the culture environment on the ability of the embryo to grow and develop into a successful pregnancy. We found that the younger the embryo was the less capable it was to cope with the stress. Also embryos that appeared normal by observation were often not and by closer examination were showing signs of stress within the cells of the embryo resulting in poor pregnancy outcomes. One of the oldest and most widely used commercial enzyme inhibitors is aspirin, Formula: C5H7NO3, which selectively inhibits one of the enzymes involved in the synthesis of molecules that trigger inflammation. you can also check out more blogs about 695-53-4

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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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Silver-catalyzed hydroamination of siloxy alkynes

(Chemical Equation Presented) New catalytic process: The silver-catalyzed hydroamination of siloxy alkynes with secondary amides furnishes silyl ketene aminals with high efficiency and excellent diastereoselectivity (see scheme), including some that are unavailable by conventional silylation methods. The reaction comprises a fast and reversible silver-alkyne complexation, followed by a rate-determining C-N bond-forming step.

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Extracurricular laboratory:new discovery of 4-Benzyloxazolidine-2,5-dione

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Synthesis of sterically hindered N-acylated amino acids from N-carboxyanhydrides

Sterically hindered N-acyl, gem-disubstituted amino acids are easily prepared via the addition of organometallic reagents to N-carboxyanhydrides (NCA). The process tolerates a wide variety of functional groups and allows the synthesis of amide products not readily accessible by traditional acylation chemistry. The existence of an isocyanate intermediate was established by in situ IR spectroscopy.

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Final Thoughts on Chemistry for 5-(Chloromethyl)oxazolidin-2-one

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Recent advances in the hofmann rearrangement and its application to natural product synthesis

C-N bond formation reactions are the most important transformations in (bio)organic chemistry because of the widespread occurrence of amines in pharmaceuticals, natural products, and biologically active compounds. The Hofmann rearrangement is a well-known method used for the preparation of primary amines from amides. But, the traditional version of the Hofmann rearrangement often gave relatively poor yields due to over-oxidation or due to the poor solubility of some amides in aqueous base, and created an enormous amount of waste products. Developments over the last two decades, in particular, have focused on refining both of these factors affecting the reaction. This review covers both the description of recent advances (2000-2019) in the Hofmann rearrangements and its applications in the synthesis of heterocycles, natural products and complex molecules of biological interest. It is revealed that organo-catalytic systems especially hypervalent iodine-based catalysts have been developed for the green and environmentally friendly conversion of carboxamides to primary amines and carbamates.

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3-halo-5-halomethyl-2-oxazolidinones and their use as microbicides

A 3-halo-5-halomethyl-2-oxazolidinone, a method of making the same and a method of using the compound as a microbicide and for controlling the growth of at least one microorganism in an aqueous system or on a surface. A process for making 5-halomethyl-2-oxazolidinone utilizing an alkali cyanate and an epihalohydrin.

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