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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. category: catalyst-ligand

Asymmetric aryl transfer of triphenylboroxin to a set of aryl aldehydes has been carried out in the presence of chiral amino alcohols derived from (S)-proline with high enantioselectivity. Substituted phenyl boroxins were also used as aryl source in asymmetric arylation of benzaldehyde.

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New modular P-chiral ligands have been prepared from commercially available (S)-alpha,alpha-diphenylprolinol. With these new types of ligands, up to 95% ee was achieved in the Rh-catalyzed asymmetric hydrogenation of functionalized olefins.

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The synthesis of a new class of bifunctional organophosphorus catalysts for the asymmetric borane reduction of prochiral ketones has been investigated. Keys to the architecture of effective catalysts are an oxazaphospholidine structural unit and a hydroxyaryl moiety. These (o-hydroxyaryl)oxazaphospholidine oxides have been successfully applied to the catalytic (2 mol-%) asymmetric borane reduction of numerous prochiral ketones with enantiomeric excesses up to 84% ee.

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The present invention provides desosamine and mycaminose analogs and nitro sugars and methods for their preparation. The invention also provides methods of cyclizing a compound of Formula (Alpha’) with glyoxal to give a nitro sugar of Formula (B). Methods for the preparation of compound of Formula (D’) are provided comprising cyclization of a nitro alcohol to give a nitro sugar and reduction and alkylation of the nitro sugar to give a desosamine, mycaminose, or an analog thereof.

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The catalytic asymmetric synthesis of densely functionalized cis-isoxazoline N-oxides was realized with novel use of an organocatalyst, (S)-2-(azidodiphenylmethyl)pyrrolidine (4e) (Tan, B.; Zhu, D.; Zhang, L.; Chua, P. J.; Zeng, X.; Zhong, G. Chem.-Eur. J. 2010, 16, 3842; Olivares-Romero, J. L.; Juaristi, E. Tetrahedron 2008, 64, 9992), via an elegant formal [4 + 1] annulation strategy using readily available 2-nitroacrylates and alpha-iodoaldehydes.

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A catalytic route to highly functionalized chiral 2-pyrazolines by an asymmetric 1,3-dipolar cycloaddition reaction of ethyl diazoacetate with alpha-substituted and alpha,beta-disubstituted acroleins has been developed; in the presence of chiral (S)-oxazaborolidinium ion 1 as catalyst, the reaction proceeded with high to excellent enantioselectivities (up to 99% ee). The Royal Society of Chemistry 2009.

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The CuBr 2 -catalyzed enantioselective allenylation of terminal alkynols with carbon chains of different lengths has been developed. Compared with (S)-alpha,alpha-diphenylprolinol, the reaction using (S)-alpha,alpha-dimethylprolinol as the chiral amine afforded optically active 1,3-disubstuted allenols with higher ee -values. Both aliphatic and aromatic aldehydes could be applied. The naturally occurring phlomic acid was synthesized in four steps from commercially available hex-5-yn-1-ol.

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New catalysts 4-10 for the asymmetric reduction of the two model ketones 13 and 14 by borane are described. These catalysts are easily prepared by reaction of the corresponding beta-amino alcohols with phenylphosphonic dichloride or alternatively by oxidation of the chiral 1,3,2-oxazaphospholidines. Enantiomeric excesses of 96% in the case of the omega-chloroacetophenone have been obtained using only 1 mol% of the optimum catalyst.

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Organocatalysts for the asymmetric reduction of ketimines are presented that function well at low catalyst loadings providing chiral amines in good yield and enantioselectivity, the latter appearing to be independent of the ketimine substrate geometry.

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The use of DPPM and DNPM as chiral modifiers in asymmetric heterogeneous catalytic hydrogenation of isophorone is reported. The effect of solvents and the concentration of reactant, modifiers and catalysts on the enantioselectivity are described. Circular dichroism spectroscopy was used to detect the interaction between the chiral modifier and the substrate.

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