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Homochiral bifunctional L-prolinamide- and L-bis-prolinamide-catalyzed asymmetric aldol reactions performed in wet solvent-free conditions.
Chirality. 2021 01; 33(1):22-36.C

Abstract

In this study, the novel bifunctional homochiral thiourea-L-prolinamides 1-4, tertiary amino-L-prolinamide 5, and bis-L-prolinamides 6 and 7 were prepared from enantiomerically pure (11R,12R)-11,12-diamino-9,10-dihydro-9,10-ethanoanthracene 8 and (11S,12S)-11,12-diamino-9,10-dihydro-9,10-ethanoanthracene ent-8. Highly enantioselective and diastereoselective aldolic intermolecular reactions (up to 95% enantiomeric excess, 93:7 anti/syn) between aliphatic ketones (20 equiv) and a range of aromatic aldehydes (1 equiv) were successfully carried out in the presence of water (10 equiv) and monochloroacetic acid (10 mol%), solvent-free conditions, at room temperature over 24 h using organocatalysts 1-7 (5 mol%). Stereoselective induction using density functional theory-based methods was consistent with the experimental data.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Huelgas G
Departamento de Ciencias Químico Biológicas, Universidad de las Americas Puebla, Cholula, Puebla, Mexico.
Somanathan R
Centro de Graduados e Investigación en Química, Tecnológico Nacional de México/Instituto Tecnológico de Tijuana, Tijuana, Baja California, Mexico.
Hernández Pérez JM
Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Puebla, Mexico.
Rojas Cabrera H
Departamento de Ciencias Químico Biológicas, Universidad de las Americas Puebla, Cholula, Puebla, Mexico.
de la Higuera Macías M
Departamento de Ciencias Químico Biológicas, Universidad de las Americas Puebla, Cholula, Puebla, Mexico.
Domínguez-Huerta A
Departamento de Ciencias Químico Biológicas, Universidad de las Americas Puebla, Cholula, Puebla, Mexico.
Sabala R
Departamento de Ciencias Químico Biológicas, Universidad de las Americas Puebla, Cholula, Puebla, Mexico.
Anaya de Parrodi C
Departamento de Ciencias Químico Biológicas, Universidad de las Americas Puebla, Cholula, Puebla, Mexico.

MeSH

AcetoneAldehydesCatalysisChemistry Techniques, SyntheticDensity Functional TheoryKetonesMolecular StructureProlineSolventsStereoisomerismThiourea

Pub Type(s)

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

Language

eng

PubMed ID

33232537

Citation

Huelgas, Gabriela, et al. "Homochiral Bifunctional L-prolinamide- and L-bis-prolinamide-catalyzed Asymmetric Aldol Reactions Performed in Wet Solvent-free Conditions." Chirality, vol. 33, no. 1, 2021, pp. 22-36.
Huelgas G, Somanathan R, Hernández Pérez JM, et al. Homochiral bifunctional L-prolinamide- and L-bis-prolinamide-catalyzed asymmetric aldol reactions performed in wet solvent-free conditions. Chirality. 2021;33(1):22-36.
Huelgas, G., Somanathan, R., Hernández Pérez, J. M., Rojas Cabrera, H., de la Higuera Macías, M., Domínguez-Huerta, A., Sabala, R., & Anaya de Parrodi, C. (2021). Homochiral bifunctional L-prolinamide- and L-bis-prolinamide-catalyzed asymmetric aldol reactions performed in wet solvent-free conditions. Chirality, 33(1), 22-36. https://doi.org/10.1002/chir.23283
Huelgas G, et al. Homochiral Bifunctional L-prolinamide- and L-bis-prolinamide-catalyzed Asymmetric Aldol Reactions Performed in Wet Solvent-free Conditions. Chirality. 2021;33(1):22-36. PubMed PMID: 33232537.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Homochiral bifunctional L-prolinamide- and L-bis-prolinamide-catalyzed asymmetric aldol reactions performed in wet solvent-free conditions. AU - Huelgas,Gabriela, AU - Somanathan,Ratnasamy, AU - Hernández Pérez,Julio M, AU - Rojas Cabrera,Haydee, AU - de la Higuera Macías,Maximiliano, AU - Domínguez-Huerta,Alejandra, AU - Sabala,Rocío, AU - Anaya de Parrodi,Cecilia, Y1 - 2020/11/24/ PY - 2020/06/22/received PY - 2020/09/25/revised PY - 2020/10/05/accepted PY - 2020/11/25/pubmed PY - 2021/9/11/medline PY - 2020/11/24/entrez KW - 1,2-diamines KW - C2-symmetry axis KW - aldol reaction KW - asymmetric organocatalysis KW - bifunctional prolinamides KW - stereoselectivity KW - wet solvent-free SP - 22 EP - 36 JF - Chirality JO - Chirality VL - 33 IS - 1 N2 - In this study, the novel bifunctional homochiral thiourea-L-prolinamides 1-4, tertiary amino-L-prolinamide 5, and bis-L-prolinamides 6 and 7 were prepared from enantiomerically pure (11R,12R)-11,12-diamino-9,10-dihydro-9,10-ethanoanthracene 8 and (11S,12S)-11,12-diamino-9,10-dihydro-9,10-ethanoanthracene ent-8. Highly enantioselective and diastereoselective aldolic intermolecular reactions (up to 95% enantiomeric excess, 93:7 anti/syn) between aliphatic ketones (20 equiv) and a range of aromatic aldehydes (1 equiv) were successfully carried out in the presence of water (10 equiv) and monochloroacetic acid (10 mol%), solvent-free conditions, at room temperature over 24 h using organocatalysts 1-7 (5 mol%). Stereoselective induction using density functional theory-based methods was consistent with the experimental data. SN - 1520-636X UR - https://www.unboundmedicine.com/medline/citation/33232537/Homochiral_bifunctional_L_prolinamide__and_L_bis_prolinamide_catalyzed_asymmetric_aldol_reactions_performed_in_wet_solvent_free_conditions_ DB - PRIME DP - Unbound Medicine ER -