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Asymmetric aldol reaction organocatalyzed by (S)-proline-containing dipeptides: improved stereoinduction under solvent-free conditions.
J Org Chem. 2011 Mar 04; 76(5):1464-7.JO

Abstract

The organocatalytic activity of the methyl ester of (S)-proline-(S)-phenylalanine, (S,S)-2, in the asymmetric aldol reaction between cyclohexanone and acetone with various aromatic aldehydes under solvent-free conditions in a ball mill has been evaluated. α,α-Dipeptide (S,S)-2 catalyzed the stereoselective formation of the expected aldol products, with higher diastereo- and enantioselectivity relative to similar reactions in solution, up to 91:9 anti:syn diastereomeric ratio and up to 95% enantiomeric excess.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Hernández JG
Departamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado Postal 14-740, 07000 México, D.F., México.
Juaristi E
No affiliation info available

MeSH

AcetoneAldehydesCatalysisCyclohexanonesDipeptidesEstersMolecular StructureProlineStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

21250720

Citation

Hernández, Josè G., and Eusebio Juaristi. "Asymmetric Aldol Reaction Organocatalyzed By (S)-proline-containing Dipeptides: Improved Stereoinduction Under Solvent-free Conditions." The Journal of Organic Chemistry, vol. 76, no. 5, 2011, pp. 1464-7.
Hernández JG, Juaristi E. Asymmetric aldol reaction organocatalyzed by (S)-proline-containing dipeptides: improved stereoinduction under solvent-free conditions. J Org Chem. 2011;76(5):1464-7.
Hernández, J. G., & Juaristi, E. (2011). Asymmetric aldol reaction organocatalyzed by (S)-proline-containing dipeptides: improved stereoinduction under solvent-free conditions. The Journal of Organic Chemistry, 76(5), 1464-7. https://doi.org/10.1021/jo1022469
Hernández JG, Juaristi E. Asymmetric Aldol Reaction Organocatalyzed By (S)-proline-containing Dipeptides: Improved Stereoinduction Under Solvent-free Conditions. J Org Chem. 2011 Mar 4;76(5):1464-7. PubMed PMID: 21250720.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric aldol reaction organocatalyzed by (S)-proline-containing dipeptides: improved stereoinduction under solvent-free conditions. AU - Hernández,Josè G, AU - Juaristi,Eusebio, Y1 - 2011/01/20/ PY - 2011/1/22/entrez PY - 2011/1/22/pubmed PY - 2011/6/8/medline SP - 1464 EP - 7 JF - The Journal of organic chemistry JO - J Org Chem VL - 76 IS - 5 N2 - The organocatalytic activity of the methyl ester of (S)-proline-(S)-phenylalanine, (S,S)-2, in the asymmetric aldol reaction between cyclohexanone and acetone with various aromatic aldehydes under solvent-free conditions in a ball mill has been evaluated. α,α-Dipeptide (S,S)-2 catalyzed the stereoselective formation of the expected aldol products, with higher diastereo- and enantioselectivity relative to similar reactions in solution, up to 91:9 anti:syn diastereomeric ratio and up to 95% enantiomeric excess. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/21250720/Asymmetric_aldol_reaction_organocatalyzed_by__S__proline_containing_dipeptides:_improved_stereoinduction_under_solvent_free_conditions_ L2 - https://doi.org/10.1021/jo1022469 DB - PRIME DP - Unbound Medicine ER -