Biomimetic asymmetric aldol reactions catalyzed by proline derivatives attached to β-cyclodextrin in water

Shen, Hai‐Min; Ji, Hongbing

doi:10.1016/j.tetlet.2012.04.140

Cited by 27 publications

(15 citation statements)

References 34 publications

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“…Synthetic peptides have the advantage of designable modularity, are readily available, and they are made up from the same chiral building blocks (amino acid residues) as enzymes. Hydrogen bonding activation has been confirmed to be an extremely powerful strategy for the construction of enantioselective transformations . We became interested designing short polar tripeptides with different positions to compare their catalytic activity in aldol reactions.…”

Section: Introductionmentioning

confidence: 99%

“…Hydrogen bonding activation has been confirmed to be an extremely powerful strategy for the construction of enantioselective transformations. [21][22][23][24] We became interested designing short polar tripeptides with different positions to compare their catalytic activity in aldol reactions. We envisaged that the hydroxyl, carboxylic, and imidazol groups after peptidation with proline would provide an additional push in the catalytic aldol process due to creation of hydrogen bonding.…”

Section: Introductionmentioning

confidence: 99%

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Various Polar Tripeptides as Asymmetric Organocatalyst in Direct Aldol Reactions in Aqueous Media

et al. 2013

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A series of tripeptide organocatalysts containing a secondary amine group and two amino acids with polar side chain units were developed and evaluated in the direct asymmetric intermolecular aldol reaction of 4-nitrobenzaldehyde and cyclohexanone. The effectiveness of short polar peptides as asymmetric catalysts in aldol reactions to attain high yields of enantio- and diastereoselective isomers were investigated. In a comparison, glutamic acid and histidine produced higher % ee and yields when they were applied as the second amino acid in short trimeric peptides. These short polar peptides were found to be efficient organocatalysts for the asymmetric aldol addition reaction in aqueous media.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Various Polar Tripeptides as Asymmetric Organocatalyst in Direct Aldol Reactions in Aqueous Media

et al. 2013

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“…They also suggested that the significant number of hydroxyl groups characteristic for CDs also plays an important role in the reduction of Pd(II) species from Pd/CaCO3. Shen and Ji [19] have reported obtaining several amino alcohol-modified β-CDs and their complexes with sodium molybdate with their following application in the asymmetric oxidation of thioanisole (Scheme 5). For the methyleneaminoethanol derivative of β-CD, a moderate enantioselectivity (56% ee) was achieved in aqueous CH3COONa-HCl buffer solution (pH 7.0).…”

Section: Methodsmentioning

confidence: 99%

“…Proposed catalytic cycle of the asymmetric oxidation of thioanisole in the presence of molybdate-methyleneaminoethanol β-CD complex, adapted from [19].…”

Section: Methodsmentioning

confidence: 99%

Cyclodextrins in Asymmetric and Stereospecific Synthesis

Macaev

Boldescu

2015

Symmetry

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Abstract:Since their discovery, cyclodextrins have widely been used as green and easily available alternatives to promoters or catalysts of different chemical reactions in water. This review covers the research and application of cyclodextrins and their derivatives in asymmetric and stereospecific syntheses, with their division into three main groups: (1) cyclodextrins promoting asymmetric and stereospecific catalysis in water; (2) cyclodextrins' complexes with transition metals as asymmetric and stereospecific catalysts; and (3) cyclodextrins' non-metallic derivatives as asymmetric and stereospecific catalysts. The scope of this review is to systematize existing information on the contribution of cyclodextrins to asymmetric and stereospecific synthesis and, thus, to facilitate further development in this direction.

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“…Recently, supported chiral organocatalysts including proline and proline derivatives on various materials to improve its recyclability have been the subject of some reviews . Usually, these materials, such as polymer, silica, ionic liquid, magnetite nanoparticles, dendrimer, and cyclodextrin, were considered as supports for the immobilization of proline and proline derivatives. In these supports, ionic liquids have attracted considerable attention based on its high thermal stability, negligible vapor pressure, high loading capacity, and easy recyclability .…”

Section: Introductionmentioning

confidence: 99%

An Ionic Liquid Containing L‐Proline Moiety as Highly Efficient and Recyclable Chiral Organocatalyst for Michael Addition

Sha

et al. 2016

Bulletin Korean Chem Soc

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A novel chiral ionic liquid containing proline moiety was synthesized. It can be used as a highly efficient and recyclable chiral organocatalyst for Michael addition of cyclohexanone with (E)‐β‐nitroalkenes in methanol at room temperature. The Michael addition affords the corresponding products in satisfactory yields of isolated products (78–98%) with high diastereoselectivities and excellent enantioselectivities (up to 98% dr and up to 99% ee). The catalyst can be recycled up to five times without any decrease in yields and stereoselectivities.

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Biomimetic asymmetric aldol reactions catalyzed by proline derivatives attached to β-cyclodextrin in water

Cited by 27 publications

References 34 publications

Various Polar Tripeptides as Asymmetric Organocatalyst in Direct Aldol Reactions in Aqueous Media

Various Polar Tripeptides as Asymmetric Organocatalyst in Direct Aldol Reactions in Aqueous Media

Cyclodextrins in Asymmetric and Stereospecific Synthesis

An Ionic Liquid Containing L‐Proline Moiety as Highly Efficient and Recyclable Chiral Organocatalyst for Michael Addition

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