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Enantioselective solvent-free synthesis of 3-alkyl-3-hydroxy-2-oxoindoles catalyzed by binam-prolinamides.
Molecules. 2015 Jul 16; 20(7):12901-12.M

Abstract

BINAM-prolinamides are very efficient catalyst for the synthesis of non-protected and N-benzyl isatin derivatives by using an aldol reaction between ketones and isatins under solvent-free conditions. The results in terms of diastereo- and enantioselectivities are good, up to 99% de and 97% ee, and higher to those previously reported in the literature under similar reaction conditions. A high variation of the results is observed depending on the structure of the isatin and the ketone used in the process. While 90% of ee and 97% ee, respectively, is obtained by using (Ra)-BINAM-l-(bis)prolinamide as catalyst in the addition of cyclohexanone and α-methoxyacetone to free isatin, 90% ee is achieved for the reaction between N-benzyl isatin and acetone using N-tosyl BINAM-l-prolinamide as catalyst. This reaction is also carried out using a silica BINAM-l-prolinamide supported catalyst under solvent-free conditions, which can be reused up to five times giving similar results.

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Authors+Show Affiliations

Bañn-Caballero A
Departamento de Química Orgánica, Instituto de Síntesis Orgánica, Universidad de Alicante, Apdo. 99, Alicante E-03080, Spain. abraham.banon@ua.es.
Flores-Ferrándiz J
Departamento de Química Orgánica, Instituto de Síntesis Orgánica, Universidad de Alicante, Apdo. 99, Alicante E-03080, Spain. jflores@ua.es.
Guillena G
Departamento de Química Orgánica, Instituto de Síntesis Orgánica, Universidad de Alicante, Apdo. 99, Alicante E-03080, Spain. gabriela.guillena@ua.es.
Nájera C
Departamento de Química Orgánica, Instituto de Síntesis Orgánica, Universidad de Alicante, Apdo. 99, Alicante E-03080, Spain. cnajera@ua.es.

MeSH

CatalysisCyclohexanonesIndolesIsatinKetonesMolecular StructureProlineStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

26193246

Citation

Bañn-Caballero, Abraham, et al. "Enantioselective Solvent-free Synthesis of 3-alkyl-3-hydroxy-2-oxoindoles Catalyzed By Binam-prolinamides." Molecules (Basel, Switzerland), vol. 20, no. 7, 2015, pp. 12901-12.
Bañn-Caballero A, Flores-Ferrándiz J, Guillena G, et al. Enantioselective solvent-free synthesis of 3-alkyl-3-hydroxy-2-oxoindoles catalyzed by binam-prolinamides. Molecules. 2015;20(7):12901-12.
Bañn-Caballero, A., Flores-Ferrándiz, J., Guillena, G., & Nájera, C. (2015). Enantioselective solvent-free synthesis of 3-alkyl-3-hydroxy-2-oxoindoles catalyzed by binam-prolinamides. Molecules (Basel, Switzerland), 20(7), 12901-12. https://doi.org/10.3390/molecules200712901
Bañn-Caballero A, et al. Enantioselective Solvent-free Synthesis of 3-alkyl-3-hydroxy-2-oxoindoles Catalyzed By Binam-prolinamides. Molecules. 2015 Jul 16;20(7):12901-12. PubMed PMID: 26193246.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective solvent-free synthesis of 3-alkyl-3-hydroxy-2-oxoindoles catalyzed by binam-prolinamides. AU - Bañn-Caballero,Abraham, AU - Flores-Ferrándiz,Jesús, AU - Guillena,Gabriela, AU - Nájera,Carmen, Y1 - 2015/07/16/ PY - 2015/06/15/received PY - 2015/07/06/revised PY - 2015/07/10/accepted PY - 2015/7/21/entrez PY - 2015/7/21/pubmed PY - 2016/5/20/medline KW - aldol KW - enantioselectivity KW - isatin KW - prolinamide KW - solvent-free KW - supported catalyst SP - 12901 EP - 12 JF - Molecules (Basel, Switzerland) JO - Molecules VL - 20 IS - 7 N2 - BINAM-prolinamides are very efficient catalyst for the synthesis of non-protected and N-benzyl isatin derivatives by using an aldol reaction between ketones and isatins under solvent-free conditions. The results in terms of diastereo- and enantioselectivities are good, up to 99% de and 97% ee, and higher to those previously reported in the literature under similar reaction conditions. A high variation of the results is observed depending on the structure of the isatin and the ketone used in the process. While 90% of ee and 97% ee, respectively, is obtained by using (Ra)-BINAM-l-(bis)prolinamide as catalyst in the addition of cyclohexanone and α-methoxyacetone to free isatin, 90% ee is achieved for the reaction between N-benzyl isatin and acetone using N-tosyl BINAM-l-prolinamide as catalyst. This reaction is also carried out using a silica BINAM-l-prolinamide supported catalyst under solvent-free conditions, which can be reused up to five times giving similar results. SN - 1420-3049 UR - https://www.unboundmedicine.com/medline/citation/26193246/Enantioselective_solvent_free_synthesis_of_3_alkyl_3_hydroxy_2_oxoindoles_catalyzed_by_binam_prolinamides_ DB - PRIME DP - Unbound Medicine ER -