Guillena, Gabriela, Hita López, María del Carmen, Nájera, Carmen
BINAM-prolinamides as recoverable catalysts in the direct aldol condensation
GUILLENA TOWNLEY, Gabriela; HITA, María del Carmen; NÁJERA DOMINGO, Carmen. "BINAM-prolinamides as recoverable catalysts in the direct aldol condensation". Tetrahedron: Asymmetry. Vol. 17, Issue 5 (6 March 2006). ISSN 0957-4166, pp. 729-733
URI: http://hdl.handle.net/10045/2575
DOI: 10.1016/j.tetasy.2006.02.004
ISSN: 0957-4166
Abstract: 
New BINAM-prolinamides were developed and tested as organocatalysts in the direct aldol condensation between aldehydes
and several aliphatic ketones. C2-symmetrical (Sa)-BINAM-L-prolinamide gives the best enantioselectivities for this transformation,
being recovered and reused after the reaction by simple extractive techniques. The reaction was performed in DMF/H2O at
0 °C to give the aldol products in up to 95% ee for acetone. For 2-butanone, the corresponding iso-regioisomers were regioselectively
obtained in up to 96% ee working in DMF at rt. In the case of cyclohexanone, dr up to 10:1 in favour of the anti products, which
were obtained in 90–93% ee, was achieved.
Keywords:Organocatalysis, Aldol, Enantioselective, Asymmetric synthesis, Amino acids, Proline
Elsevier
info:eu-repo/semantics/article