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Molecules 2015, 20(7), 12901-12912; doi:10.3390/molecules200712901

Enantioselective Solvent-Free Synthesis of 3-Alkyl-3-hydroxy-2-oxoindoles Catalyzed by Binam-Prolinamides

Departamento de Química Orgánica, Instituto de Síntesis Orgánica, Universidad de Alicante, Apdo. 99, Alicante E-03080, Spain
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Academic Editor: Raquel Herrera
Received: 15 June 2015 / Revised: 6 July 2015 / Accepted: 10 July 2015 / Published: 16 July 2015
(This article belongs to the Collection Recent Advances in Organocatalysis)
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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. View Full-Text
Keywords: isatin; aldol; enantioselectivity; solvent-free; prolinamide; supported catalyst isatin; aldol; enantioselectivity; solvent-free; prolinamide; supported catalyst
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Bañn-Caballero, A.; Flores-Ferrándiz, J.; Guillena, G.; Nájera, C. Enantioselective Solvent-Free Synthesis of 3-Alkyl-3-hydroxy-2-oxoindoles Catalyzed by Binam-Prolinamides. Molecules 2015, 20, 12901-12912.

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