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Enantioselective direct aldol reaction of α-keto esters catalyzed by (S(a))-binam-D-prolinamide under quasi solvent-free conditions.
Org Biomol Chem. 2012 May 28; 10(20):4029-35.OB

Abstract

(S(a))-Binam-D-prolinamide (20 mol%), instead of (S(a))-binam-L-prolinamide, in combination with chloroacetic acid (100 mol%) is an efficient organocatalyst for the direct aldol reaction between α-keto esters as electrophiles and alkyl and α-functionalised ketones, under quasi solvent-free conditions, providing access to highly functionalised chiral quaternary γ-keto α-hydroxyesters with up to 92% ee.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Viózquez SF
Dpto. Química Orgánica and Instituto de Síntesis Orgánica, Universidad de Alicante, Apdo. 99, E-03080 Alicante, Spain.
Bañón-Caballero A
No affiliation info available
Guillena G
No affiliation info available
Nájera C
No affiliation info available
Gómez-Bengoa E
No affiliation info available

MeSH

CatalysisEstersKetonesModels, MolecularMolecular StructureProlineSolventsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

22514086

Citation

Viózquez, Santiago F., et al. "Enantioselective Direct Aldol Reaction of Α-keto Esters Catalyzed By (S(a))-binam-D-prolinamide Under Quasi Solvent-free Conditions." Organic & Biomolecular Chemistry, vol. 10, no. 20, 2012, pp. 4029-35.
Viózquez SF, Bañón-Caballero A, Guillena G, et al. Enantioselective direct aldol reaction of α-keto esters catalyzed by (S(a))-binam-D-prolinamide under quasi solvent-free conditions. Org Biomol Chem. 2012;10(20):4029-35.
Viózquez, S. F., Bañón-Caballero, A., Guillena, G., Nájera, C., & Gómez-Bengoa, E. (2012). Enantioselective direct aldol reaction of α-keto esters catalyzed by (S(a))-binam-D-prolinamide under quasi solvent-free conditions. Organic & Biomolecular Chemistry, 10(20), 4029-35. https://doi.org/10.1039/c2ob25224d
Viózquez SF, et al. Enantioselective Direct Aldol Reaction of Α-keto Esters Catalyzed By (S(a))-binam-D-prolinamide Under Quasi Solvent-free Conditions. Org Biomol Chem. 2012 May 28;10(20):4029-35. PubMed PMID: 22514086.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective direct aldol reaction of α-keto esters catalyzed by (S(a))-binam-D-prolinamide under quasi solvent-free conditions. AU - Viózquez,Santiago F, AU - Bañón-Caballero,Abraham, AU - Guillena,Gabriela, AU - Nájera,Carmen, AU - Gómez-Bengoa,Enrique, Y1 - 2012/04/18/ PY - 2012/4/20/entrez PY - 2012/4/20/pubmed PY - 2012/8/16/medline SP - 4029 EP - 35 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 10 IS - 20 N2 - (S(a))-Binam-D-prolinamide (20 mol%), instead of (S(a))-binam-L-prolinamide, in combination with chloroacetic acid (100 mol%) is an efficient organocatalyst for the direct aldol reaction between α-keto esters as electrophiles and alkyl and α-functionalised ketones, under quasi solvent-free conditions, providing access to highly functionalised chiral quaternary γ-keto α-hydroxyesters with up to 92% ee. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/22514086/Enantioselective_direct_aldol_reaction_of_α_keto_esters_catalyzed_by__S_a___binam_D_prolinamide_under_quasi_solvent_free_conditions_ L2 - https://doi.org/10.1039/c2ob25224d DB - PRIME DP - Unbound Medicine ER -