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Asymmetric aldol reaction catalyzed by a heterogenized proline on a mesoporous support. The role of the nature of solvents.
J Org Chem. 2007 Nov 23; 72(24):9353-6.JO

Abstract

A heterogenized (S)-proline on mesoporous support MCM-41 catalyzes the asymmetric aldol reaction in a wide range of solvents. The progress of the reaction is dependent on the nature of the solvent. Reactions proceed more efficiently in hydrophilic polar solvents; however, the addition of a small amount of water has a positive effect on the rate and the stereoselectivity of the reaction performed in hydrophobic toluene. The reaction under heterogeneous conditions has also been performed on chiral aldehydes, furnishing useful intermediates for the synthesis of azasugars.

Authors+Show Affiliations

Doyagüez EG
Instituto de Química OrgAnica General, CSIC, Juan de la Cierva 3, 28006, Madrid, Spain.
Calderón F
No affiliation info available
Sanchez F
No affiliation info available
Fernandez-Mayoralas A
No affiliation info available

MeSH

AldehydesAza CompoundsCarbohydratesCatalysisHydrophobic and Hydrophilic InteractionsModels, ChemicalProlineSilicon DioxideSolventsToluene

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

17958368

Citation

Doyagüez, Elisa G., et al. "Asymmetric Aldol Reaction Catalyzed By a Heterogenized Proline On a Mesoporous Support. the Role of the Nature of Solvents." The Journal of Organic Chemistry, vol. 72, no. 24, 2007, pp. 9353-6.
Doyagüez EG, Calderón F, Sanchez F, et al. Asymmetric aldol reaction catalyzed by a heterogenized proline on a mesoporous support. The role of the nature of solvents. J Org Chem. 2007;72(24):9353-6.
Doyagüez, E. G., Calderón, F., Sanchez, F., & Fernandez-Mayoralas, A. (2007). Asymmetric aldol reaction catalyzed by a heterogenized proline on a mesoporous support. The role of the nature of solvents. The Journal of Organic Chemistry, 72(24), 9353-6.
Doyagüez EG, et al. Asymmetric Aldol Reaction Catalyzed By a Heterogenized Proline On a Mesoporous Support. the Role of the Nature of Solvents. J Org Chem. 2007 Nov 23;72(24):9353-6. PubMed PMID: 17958368.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric aldol reaction catalyzed by a heterogenized proline on a mesoporous support. The role of the nature of solvents. AU - Doyagüez,Elisa G, AU - Calderón,Félix, AU - Sanchez,Félix, AU - Fernandez-Mayoralas,Alfonso, Y1 - 2007/10/24/ PY - 2007/10/26/pubmed PY - 2008/2/27/medline PY - 2007/10/26/entrez SP - 9353 EP - 6 JF - The Journal of organic chemistry JO - J Org Chem VL - 72 IS - 24 N2 - A heterogenized (S)-proline on mesoporous support MCM-41 catalyzes the asymmetric aldol reaction in a wide range of solvents. The progress of the reaction is dependent on the nature of the solvent. Reactions proceed more efficiently in hydrophilic polar solvents; however, the addition of a small amount of water has a positive effect on the rate and the stereoselectivity of the reaction performed in hydrophobic toluene. The reaction under heterogeneous conditions has also been performed on chiral aldehydes, furnishing useful intermediates for the synthesis of azasugars. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/17958368/Asymmetric_aldol_reaction_catalyzed_by_a_heterogenized_proline_on_a_mesoporous_support__The_role_of_the_nature_of_solvents_ L2 - https://doi.org/10.1021/jo070992s DB - PRIME DP - Unbound Medicine ER -