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Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 112068-01-6, molcular formula is C17H19NO, introducing its new discovery. Safety of (S)-Diphenyl(pyrrolidin-2-yl)methanol

An organocatalytic Michael reaction of 2-nitro methylene imidazolidines to alpha,beta-unsaturated aldehydes followed by acetal-amination affords hexahydroimidazo[1,2-a]pyridines in high yields and with moderate to excellent enantioselectivity. The utility of the reaction was illustrated by a one-step transformation to Paichongding, an insecticide of the neonicotinoid family.

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The development of zinc-mediated and -catalyzed asymmetric propargylations of trifluoromethyl ketones with a propargyl borolane and the N-isopropyl-l-proline ligand is presented. The methodology provided moderate to high stereoselectivity and was successfully applied on a multikilogram scale for the synthesis of the Glucocorticoid agonist BI 653048. A mechanism for the boron-zinc exchange with a propargyl borolane is proposed and supported by modeling at the density functional level of theory. A water acceleration effect on the zinc-catalyzed propargylation was discovered, which enabled a catalytic process to be achieved. Reaction progress analysis supports a predominately rate limiting exchange for the zinc-catalyzed propargylation. A catalytic amount of water is proposed to generate an intermediate that catalyzes the exchange, thereby facilitating the reaction with trifluoromethyl ketones.

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Metal catalyst and ligand design,
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Identification of a novel catalyst-allenoate pair allows enantioselective [2+2] cycloaddition of alpha-methylstyrene. To understand the origin of selectivity, a detailed mechanistic investigation was conducted. Herein, two competing reaction pathways are proposed, which operate simultaneously and funnel the alkenes to the same axially chiral cyclobutanes. In agreement with the Woodward-Hoffmann rules, this mechanistic curiosity can be rationalized through a unique symmetry operation that was elucidated by deuteration experiments. In the case of 1,1-diarylalkenes, distal communication between the catalyst and alkene is achieved through subtle alteration of electronic properties and conformation. In this context, a Hammett study lends further credibility to a concerted mechanism. Thus, extended scope exploration, including beta-substitution on the alkene to generate two adjacent stereocenters within the cyclobutane ring, is achieved in a highly stereospecific and enantioselective fashion (33 examples, up to >99:1 er).

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The synthesis of a number of novel homochiral prolinol N-oxide derivatives is described. Several of these were found to catalyse the borane reduction of alpha-chloroacetophenone to (S)-2-chloro-1-phenylethanol in excellent chemical yield and in 96% ee.

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Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 112068-01-6, molcular formula is C17H19NO, introducing its new discovery. Quality Control of: (S)-Diphenyl(pyrrolidin-2-yl)methanol

The diphenylmethyl group is a molecular propeller that can detect the chirality of a nearby stereogenic center through electronic circular dichroism spectra, within the short wavelength region of the phenyl 1B transitions (190-200 nm). A positive exciton Cotton effect was associated with a positive (P) helicity of the diphenylmethyl group, while the opposite was true for M helicity. Higher helicity discrimination was observed in the presence of a hydroxy group (in hydroxydiphenylmethyl derivatives) which formed an intramolecular hydrogen bond, thus reducing the number of accessible conformers of the molecule. We found that the hydroxydiphenylmethyl groups in chiral tartaric acid TADDOL derivatives were preferably heterohelical (P, M).

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Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 112068-01-6, molcular formula is C17H19NO, introducing its new discovery. Application In Synthesis of (S)-Diphenyl(pyrrolidin-2-yl)methanol

We employed the membrane of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) liposomes suspended in water as a microenvironment for carrying out the organocatalytic epoxidation of an alpha-alkylidene oxindole. The reaction proceeds smoothly and displays diastereo- and enantio-selectivity that differs from what is achieved under bulk solution conditions. The potential of organocatalytic approaches for synthetic transformations in aqueous phase in the presence of dispersed membranes is briefly discussed.

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Resolution of the racemic amino alcohol derivatives 1-6 is readily achieved to obtain enantiomerically enriched compounds using chiral 1,1?-bi-2-naphthol and boric acid in solvents such as CH3-CN, THF, and MeOH. Purification of the diastereomeric mixture 7 has also been carried out following this method. The corresponding intermediate ammonium borate complexes were also characterized by X-ray diffraction methods.

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A study was conducted to demonstrate highly enantioselective synthesis of beta-amino acid derivatives by the Lewis base catalyzed hydrosilylation of betaenamino esters. It was found that these catalyst and its analogue displayed excellent activities and enantioselectivities in promoting hydrosilylation of N-aryl beta-enamino esters. N-picolinoylpyrrolidine derivatives and N-picolioylephedrine were also evaluated in hydrosilylation of (Z)-methyl 3-phenyl-3-(phenylamino)acrylate. The generality of the Lewis base organocatalyzed hydrosilylation of various beta-enamino esters were examined under the optimized conditions. It was observed that the catalytic system exhibited a high sensitivity to the N-substituents, while all the N-aryl beta-enamino esters underwent the hydrosilylation smoothly to give corresponding beta-amino esters.

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Metal catalyst and ligand design,
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This paper reports a new method for the generation of chiral Lewis superacids by protonation of a non-Lewis acidic oxazaborolidine (1) with triflic acid. The resulting cationic species (3) are powerful and highly enantioselective catalysts for the Diels-Alder reaction of various 1,3-dienes with alpha,beta-enals. An optimization study (see Table 1) led to the selection of reaction conditions and catalysts (6A and 6B) which are very effective. The reactions are simple to conduct, reproducible, and economical, since only ca. 6 mol% of catalyst is required. In addition, the chiral catalyst precursor is readily recovered for reuse (>95% efficiency) and is commercially available. The broad scope of the process is documented by the 14 examples listed in Table 2. The absolute stereochemical course of the Diels-Alder reactions catalyzed by 6A and 6B was successfully predicted on the basis of the mechanistic principles which have recently been formulated for this type of catalytic enantioselective reaction involving re-face attack by the diene on complex 7. The mode of generation of Lewis superacids 6A and 6B allows an approximate comparison (or scale) connecting the catalytic power Lewis and protic acids. Copyright

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Metal catalyst and ligand design,
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Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 112068-01-6, molcular formula is C17H19NO, introducing its new discovery. Recommanded Product: (S)-Diphenyl(pyrrolidin-2-yl)methanol

Simple enantioselective routes to the two key intermediates shown above (at center) for the synthesis of laurenditerpenol have been developed using a Diels-Alder step and the same catalyst system for each.

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Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI