enantioselective solvent-free synthesis of 3-alkyl-3-hydroxy-2-oxoindoles catalyzed by binam-prolinamides
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ID: 211875
2015
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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.
| Reference Key |
ban-caballero2015moleculesenantioselective
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|---|---|
| Authors | ;Abraham Bañn-Caballero;Jesús Flores-Ferrándiz;Gabriela Guillena;Carmen Nájera |
| Journal | Journal of ethnopharmacology |
| Year | 2015 |
| DOI |
10.3390/molecules200712901
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