Enantioselective reduction of ketoimines promoted by easily available (S)-proline derivatives

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Enantioselective reduction of ketoimines promoted by easily available (S)-proline derivatives

The behavior of readily synthesized and even commercially available (S)-proline derivatives, was studied in the trichlorosilane-mediated reduction of ketoimines. A small library of structurally and electronically modified chiral Lewis bases was considered; such compounds were shown to promote the enantioselective reduction of different substrates in good chemical yields. In the HSiCl3 addition ...

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Recent progress in Lewis acid–Lewis base bifunctional asymmetric catalysis*

Two enantioselective cyanation reactions, the Strecker reaction of ketoimines and the Reissert reaction of pyridine derivatives, promoted by Lewis acid–Lewis base bifunctional asymmetric catalysts are described.

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L-Proline catalyzed synthesis of Betti bases and biscoumarin derivatives

The direct three component modified Mannich reaction via condensation of aldehydes, 2-naphthol or 2,7-naphthalendiol and piperidine to generate Betti bases has been carried out over L-proline (20 mol%) with high efficiency under solvent free conditions at 70 OC. Also, the reaction of aromatic aldehyde and 4-hydroxycoumarin in the presence of L-proline (20 mol%) in the ethanol under reflux condi...

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L-Proline catalyzed synthesis of Betti bases and biscoumarin derivatives

The direct three component modified Mannich reaction via condensation of aldehydes, 2-naphthol or 2,7-naphthalendiol and piperidine to generate Betti bases has been carried out over L-proline (20 mol%) with high efficiency under solvent free conditions at 70 OC. Also, the reaction of aromatic aldehyde and 4-hydroxycoumarin in the presence of L-proline (20 mol%) in the ethanol under reflux condi...

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Enantioselective organocatalytic hydride reduction.

The first enantioselective organocatalytic hydride reduction has been accomplished. The use of iminium catalysis has provided a new organocatalytic strategy for the enantioselective reduction of beta,beta-substituted alpha,beta-unsaturated aldehydes to generate beta-stereogenic aldehydes. The use of imidazolidinone 2 as the asymmetric catalyst has been found to mediate the transfer of hydrogen ...

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ژورنال

عنوان ژورنال: Beilstein Journal of Organic Chemistry

سال: 2013

ISSN: 1860-5397

DOI: 10.3762/bjoc.9.71