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Boosting the hydrolytic stability of phosphite ligand in hydroformylation by the construction of superhydrophobic porous framework

The development of a catalyst that delivers high activities and selectivities with excellent durability is of great importance. Numerous efficient catalysts suffer from the inherent hydrolysis liabilities, plaguing their practical applications. Herein, we show that this challenge can be tackled by constructing them into superhydrophobic porous frameworks, as exemplified by a water-sensitive phosphite ligand, tris(2-tert-butylphenyl) phosphite. The efficiency and long-term stability of the developed system are remarkably high in the hydroformylation of internal olefins after metalation with Rh species, superior to the corresponding homogeneous analogues. The significantly boosted hydrolytic stability allows for catalytic transformations using water as a green solvent, which not only facilitates the isolation of the products, but also furnishes the aldehydes with higher regioselectivities for the desired linear form in comparison with that operated under benchmark conditions using toluene as a reaction medium. Given these promising results, we anticipate the strategy advanced herein will form the basis for constructive perspectives in the enhancement of the water resistance of catalysts and the development of high performance hydroformylation catalysts.

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Disulfide-Bridged Peptides That Mediate Enantioselective Cycloadditions through Thiyl Radical Catalysis

An enantioselective vinylcyclopropane ring-opening/cycloaddition cascade is described. The active thiyl radical catalysts are generated in situ via UV light-promoted homolysis of cystine-based dimers. Amide-functionalization of the peptide at the 4-proline position is essential for effective asymmetric induction. Stereochemical communication is dependent on steric interactions with this substituent that are enforced by H-bonding to the peptide backbone.

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Enantioselective synthesis of stephacidin B

We describe an enantioselective synthetic route to the antiproliferative alkaloid stephacidin B (1) proceeding in 18 steps and 4.0% yield from 4,4-(ethylenedioxy)-2,2-dimethylcyclohexanone (3). Key features of the synthetic sequence include the use of the Corey-Bakshi-Shibata (CBS) reduction to introduce asymmetry early in the synthetic route, use of the novel electrophile N-(tert-butoxycarbonyl)-5-(isopropylsulfonyloxymethyl)-2,3-dihydropyrrole in a stereoselective enolate alkylation, a diastereoselective Strecker-type addition of hydrogen cyanide to an N-Boc enamine substrate in the solvent hexafluoroisopropanol, platinum-catalyzed nitrile hydrolysis under neutral conditions, cyclization of an acylamino radical intermediate to form the diketopiperazine core of stephacidin B, and implementation of a convergent procedure for introduction of the key 3-alkylidene-3H-indole 1-oxide functional group in the final stage of the route to prepare the structure 2, previously proposed to be the fungal metabolite avrainvillamide (17 steps, 4.2% yield). We observed that synthetic (-)-2 dimerized in the presence of triethylamine to form (+)-stephacidin B (>95%). We also obtained evidence that 2 can form 1 under mild conditions, and that 2 reacts with nucleophiles, such as methanol, by conjugate addition. Copyright

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Synthesis, Application and Kinetic Studies of Chiral Phosphite-Oxazoline Palladium Complexes as Active and Selective Catalysts in Intermolecular Heck Reactions

This study identifies new phosphite-oxazoline ligands that have been successfully applied in the palladium-catalyzed intermolecular asymmetric Heck reaction. The design of the new phosphite-oxazoline ligands derives from a previous successful generation of phosphine-oxazoline ligands, by replacing the phosphine group with several pi-acceptor biaryl phosphite moieties. With these simple modifications, the new phosphite-based ligands, unlike previous phosphine-oxazoline, not only present a modular design with numerous potential phosphite groups available, but they are also air-stable solids, which can be made in the same number of synthetic steps as the phosphine analogues. The substitution of the phosphine by a biaryl phosphite group extended the range of substrates and triflates sources that can be coupled with regio-, enantioselectivities and activities comparable to the few best ones reported. In addition, the ligands that provided the best selectivities contained an isopropyl oxazoline moiety instead of the tert-butyl group found in the related phosphine-oxazoline ligands, which is made from a much more expensive precursor. In this paper we have also carried out kinetic studies and a Hammett plot analysis to determine the rate determining step of this system in the regime of interest. We suggest a likely explanation for the fast Heck reaction of the phosphite-oxazoline catalysts. (Figure presented.).

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Catalytic generation and selective heterocoupling of two electron-rich alkenes

Complex heterocyclic products were synthesized from simple alkynamine and alkynol derivatives in a double cycloisomerization/heterodimerization cascade reaction (see scheme). The reaction includes the heterocoupling reaction of two different electron-rich alkenes and leads to the formation of four new bonds and three stereocenters (two of them quaternary). Copyright

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Asymmetric Hydroformylation of Heterocyclic Olefins Catalyzed by Chiral Phosphine-Phosphite-Rh(I) Complexes

Asymmetric hydroformylation of heterocyclic olefins catalyzed by phosphine-phosphite-Rh(I) complexes has been investigated. Hydroformylation of symmetrical heterocyclic olefins such as 2,5-dihydrofuran, 3-pyrroline derivatives, and 4,7-dihydro-1,3-dioxepin derivatives afforded the optically active aldehydes as single products in 64-76% ee. Unsymmetrical substrates such as 2,3-dihydrofuran and N-(tert-butoxycarbonyl)-2-pyrroline gave a mixture of regioisomers. From N-(tert-butoxycarbonyl)-2-pyrroline was obtained N-(tert-butoxycarbonyl)pyrrolidine-2-carbaldehyde in 97% ee. The hydroformylation products from 2,5-dihydrofuran and N-(tert-butoxycarbonyl)-3-pyrroline have the opposite configurations to those from 2,3-dihydrofuran and N-(tert-butoxycarbonyl)-2-pyrroline, respectively, with the same catalyst. The new phosphine-phosphite ligand (R,S)-3,3?-Me2-BINAPHOS [= (A)-2-(diphenylphosphino)-1,1?-binaphthalen-2?-yl (S)-3,3?-dimethyl-1,1?-binaphthalene-2,2?-diyl phosphite] was prepared and its hydridorhodium complex was characterized by NMR spectroscopy. Using (R,S)-3,3?-Me2-BINAPHOS as a ligand, the enantioselectivity was improved for some substrates. In addition, higher catalytic activity was observed with this ligand for most of the substrates employed.

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Free-radical carbo-alkenylation of enamides and ene-carbamates

The addition of xanthates and vinyldisulfones across the double bond of enamides and ene-carbamates provides access to the corresponding three-component adducts in good to excellent yields with a high level of diastereocontrol in cyclic systems. This strategy illustrates a complementary reactivity for these versatile olefins and extends their scope of application.

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Aza-Peptide Michael Acceptors: A New Class of Inhibitors Specific for Caspases and Other Clan CD Cysteine Proteases

Aza-peptide Michael acceptors are a new class of irreversible inhibitors that are highly potent and specific for clan CD cysteine proteases. The aza-Asp derivatives were specific for caspases, while aza-Asn derivatives were effective legumain inhibitors. Aza-Lys and aza-Orn derivatives were potent inhibitors of gingipain K and clostripain. Aza-peptide Michael acceptors showed no cross reactivity toward papain, cathepsin B, and calpain.

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Access to cyclic: Gem-difluoroacyl scaffolds via electrochemical and visible light photocatalytic radical tandem cyclization of heteroaryl chlorodifluoromethyl ketones

A variety of unprecedented scaffolds containing a difluoroacyl moiety were obtained in moderate to good yields, with excellent diastereoselectivity, via electrochemical or photochemical activation of difluoroacyl heteroaryles with a series of olefinic substrates.

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QUINOXALINE AND PYRIDOPYRAZINE DERIVATIVES AS PI3KBETA INHIBITORS

The present invention relates to substituted quinoxaline and pyridopyrazine derivatives of Formula (I) wherein the variables have the meaning defined in the claims. The compounds according to the present invention are useful as pI3Kbeta inhibitors. The invention further relates to pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.

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