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Solvent-Free Enantioselective Friedländer Condensation with Wet 1,1′-Binaphthalene-2,2′-diamine-Derived Prolinamides as Organocatalysts

Abraham Bañón-Caballero, Gabriela Guillena* and Carmen Nájera*

*Departamento de Química Orgánica e Instituto de Síntesis Orgánica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, E-03080 Alicante, Spain, Email: gabriela.guillenaua.es, cnajeraua.es

A. Bañón-Caballero, G. Guillena, C. Nájera, J. Org. Chem., 2013, 78, 5349-5356.

DOI: 10.1021/jo400522m (free Supporting Information)



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Abstract

Wet unsupported and supported 1,1′-binaphthalene-2,2′-diamine (BINAM) derived prolinamides are efficient organocatalysts under solvent-free conditions at room temperature for the synthesis of chiral tacrine analogues in good yields and excellent enantioselectivies. The Friedländer reaction involved in this process takes place with a broad range of cyclohexanone derivatives as well as 2-aminoaromatic aldehydes.

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Key Words

Friedländer Synthesis, Organocatalysis, Green Chemistry


ID: J42-Y2013