Asymmetric Aldol Reaction Using Immobilized Proline on Mesoporous Support

Calderón, Félix; Fernández, Raquel M.; Sánchez, Félix; Fernández-Mayoralas, Alfonso

doi:10.1002/adsc.200505058

Cited by 123 publications

(41 citation statements)

References 28 publications

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“…They were isolated with a high degree of anti-diastereoselectivity. 49,50,54 These results demonstrate the feasibility of a metallorganic approach to aldol adducts of hydroxaycetone. Moreover, the obtained syn-configured aldol adducts make this method to a valuable addition to the well-established anti-selective proline-catalysis.…”

Section: Resultsmentioning

confidence: 60%

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Multinuclear enantiopure titanium self‐assembly complexes—synthesis, characterization and application to organic synthesis

Schetter

Stosiek

Ziemer

et al. 2007

Applied Organom Chemis

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Hexa-and nonanuclear titanium complexes were obtained by self-assembly of titanium(IV)-tertbutoxide and D-mandelic acid. Suitable single crystals of these complexes were characterized by X-ray structure analysis. When used with these complexes, aldol adducts were isolated with a high degree of regioselectivity in direct aldol additions of aromatic and aliphatic aldehydes to functionalized unsymmetrical ketones. High syn-diastereoselectivities were obtained in aldol additions of enolizable aldehydes with hydroxyacetone and methoxyacetone.

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Section: Resultsmentioning

confidence: 60%

“…Moreover, the obtained syn-configured aldol adducts make this method to a valuable addition to the well-established anti-selective proline-catalysis. 49,50,55 Methoxyacetone is also a suitable substrate for this approach. When used with methoxyacetone 23 the observed syn-preference was intensified (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Multinuclear enantiopure titanium self‐assembly complexes—synthesis, characterization and application to organic synthesis

Schetter

Stosiek

Ziemer

et al. 2007

Applied Organom Chemis

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“…dendrimers, 153 mesoporous materials, 154 polyelectrolytes, 155 and layered double hydroxides. 156 Although their utility is somewhat limited, other miscellaneous catalysts have been reported (Chart 4):…”

Section: Polymer-supported Catalysts and Othersmentioning

confidence: 99%

Organocatalytic Asymmetric Synthesis Using Proline and Related Molecules. Part 2.

Kotsuki¹,

Ikishima²,

Okuyama³

2008

HETEROCYCLES

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-Organocatalytic asymmetric synthesis has been extensively studied and several important procedures for preparing optically active organic compounds have been developed. Research in this area has progressed rapidly in the last ten years. This review addresses the most significant advances in asymmetric synthesis using proline and related chiral organocatalysts mainly focusing on aldol reactions from the viewpoint of synthetic interests. This includes (1) proline-catalyzed aldol reactions, (2) proline-related chiral catalysts, and (3) other types of amino acid catalysts.

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“…Proline, which is stable and easy handle, was usually immobilized onto organic and inorganic supports by postgrafting or the co-condensation method. [27][28][29][30][31] However, the immobilization of prolinamide, which is more expensive and a more efficient organocatalyst, is rarely reported. [32,33] Therefore the preparation of prolinamidefunctionalized heterogeneous catalysts is interesting from both an academic and economic point of view.…”

Section: Introductionmentioning

confidence: 99%

Chirally Functionalized Hollow Nanospheres Containing L‐Prolinamide: Synthesis and Asymmetric Catalysis

Gao

Liu

Tang

et al. 2010

Chemistry A European J

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Chirally functionalized hollow nanospheres with different surface properties were successfully synthesized by co-condensation of (2S,1'R,2'R)-N-tert-butyloxycarbonylpyrrolidine-2-carboxylic acid [2'-(4-trimethoxysilylbenzylamide)cyclohexyl] amide with 1,2-bis(trimethoxysilyl)ethane or tetramethoxysilane using F127 (EO(106)PO(70)EO(106)) as surfactant in water. The TEM and N(2) sorption characterizations show that the particle size of the hollow nanosphere is 15-21 nm with a core diameter of 10-16 nm. These L-prolinamide-functionalized hollow nanospheres are highly efficient solid catalysts for the direct asymmetric aldol reaction between cyclohexanone and aromatic aldehydes. It was found that the addition of water in the reaction system not only enhanced the catalytic activity but also increased the enantioselectivity, which is probably due to the enhanced hydrogen bond between the amide oxygen atom and the hydroxyl group of water. Moreover, the catalytic activity increases sharply as the surface hydrophobicity of the hollow nanospheres increases. These hollow nanospheres are quite stable and can be reused with almost the same enantioselectivity and only a slight decrease in catalytic activity.

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Asymmetric Aldol Reaction Using Immobilized Proline on Mesoporous Support

Cited by 123 publications

References 28 publications

Multinuclear enantiopure titanium self‐assembly complexes—synthesis, characterization and application to organic synthesis

Multinuclear enantiopure titanium self‐assembly complexes—synthesis, characterization and application to organic synthesis

Organocatalytic Asymmetric Synthesis Using Proline and Related Molecules. Part 2.

Chirally Functionalized Hollow Nanospheres Containing L‐Prolinamide: Synthesis and Asymmetric Catalysis

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