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Proline-beta(3)-amino-ester dipeptides as efficient catalysts for enantioselective direct aldol reaction in aqueous medium.
J Org Chem. 2009 Dec 18; 74(24):9562-5.JO

Abstract

Dipeptides obtained from l-proline and beta(3)-l-amino acids are reported to catalyze enantioselective direct aldol reaction in aqueous medium, leading to significant anti:syn diastereomeric ratios and enantiomeric excesses. The simple introduction of a polar substituent at the C-2 position of the beta(3)-l-amino acid was also found to enhance appreciably both diastereo- and enantioselectivity of the catalyst.

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Publisher Full Text (DOI)

Authors+Show Affiliations

De Nisco M
Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, Via Cintia, 4 Napoli 80126, Italy. denisco@unina.it
Pedatella S
No affiliation info available
Ullah H
No affiliation info available
Zaidi JH
No affiliation info available
Naviglio D
No affiliation info available
Ozdamar O
No affiliation info available
Caputo R
No affiliation info available

MeSH

AldehydesBenzaldehydesCatalysisChromatography, High Pressure LiquidCyclohexanonesDipeptidesEstersHydrophobic and Hydrophilic InteractionsMagnetic Resonance SpectroscopyProlineStereoisomerismTryptophanTyrosineWater

Pub Type(s)

Journal Article

Language

eng

PubMed ID

19938836

Citation

De Nisco, Mauro, et al. "Proline-beta(3)-amino-ester Dipeptides as Efficient Catalysts for Enantioselective Direct Aldol Reaction in Aqueous Medium." The Journal of Organic Chemistry, vol. 74, no. 24, 2009, pp. 9562-5.
De Nisco M, Pedatella S, Ullah H, et al. Proline-beta(3)-amino-ester dipeptides as efficient catalysts for enantioselective direct aldol reaction in aqueous medium. J Org Chem. 2009;74(24):9562-5.
De Nisco, M., Pedatella, S., Ullah, H., Zaidi, J. H., Naviglio, D., Ozdamar, O., & Caputo, R. (2009). Proline-beta(3)-amino-ester dipeptides as efficient catalysts for enantioselective direct aldol reaction in aqueous medium. The Journal of Organic Chemistry, 74(24), 9562-5. https://doi.org/10.1021/jo902106r
De Nisco M, et al. Proline-beta(3)-amino-ester Dipeptides as Efficient Catalysts for Enantioselective Direct Aldol Reaction in Aqueous Medium. J Org Chem. 2009 Dec 18;74(24):9562-5. PubMed PMID: 19938836.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Proline-beta(3)-amino-ester dipeptides as efficient catalysts for enantioselective direct aldol reaction in aqueous medium. AU - De Nisco,Mauro, AU - Pedatella,Silvana, AU - Ullah,Hidayat, AU - Zaidi,Javid H, AU - Naviglio,Daniele, AU - Ozdamar,Ozgür, AU - Caputo,Romualdo, PY - 2009/11/27/entrez PY - 2009/11/27/pubmed PY - 2010/3/20/medline SP - 9562 EP - 5 JF - The Journal of organic chemistry JO - J Org Chem VL - 74 IS - 24 N2 - Dipeptides obtained from l-proline and beta(3)-l-amino acids are reported to catalyze enantioselective direct aldol reaction in aqueous medium, leading to significant anti:syn diastereomeric ratios and enantiomeric excesses. The simple introduction of a polar substituent at the C-2 position of the beta(3)-l-amino acid was also found to enhance appreciably both diastereo- and enantioselectivity of the catalyst. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/19938836/Proline_beta_3__amino_ester_dipeptides_as_efficient_catalysts_for_enantioselective_direct_aldol_reaction_in_aqueous_medium_ L2 - https://doi.org/10.1021/jo902106r DB - PRIME DP - Unbound Medicine ER -