期刊
MOLECULES
卷 20, 期 7, 页码 12901-12912出版社
MDPI AG
DOI: 10.3390/molecules200712901
关键词
isatin; aldol; enantioselectivity; solvent-free; prolinamide; supported catalyst
资金
- Ministerio de Economia y Competitividad (MINECO) [CTQ2010-20387]
- Ministerio de Economia y Competitividad (Consolider INGENIO) [CSD2007-0006]
- FEDER
- Generalitat Valenciana [Prometeo/2009/039]
- University of Alicante
- EU (ORCA action) [CM0905]
- Spanish MICINN [FPU AP2009-3601]
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 (R-a)-BINAM-L-(bis) prolinamide as catalyst in the addition of cyclohexanone and alpha-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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