Combined Role of the Asymmetric Counteranion-Directed Catalysis (ACDC) and Ionic Liquid Effect for the Enantioselective Biginelli Multicomponent Reaction

Haline G. O. Alvim, Danielle L. J. Pinheiro, Valter H. Carvalho-Silva, Mariana Fioramonte, Fabio C. Gozzo, Wender A. da Silva, Giovanni W. Amarante*, Brenno A. D. Neto*

*Campus Universitário São Pedro, Juiz de Fora, Minas Gerais 36036-900; Campus Universitário Darcy Ribeiro, P.O. Box 4478, Brasília, Distrito Federal 70904-970, Brazil, Email: giovanni.amaranteufjf.edu.br, brenno.ipigmail.com

H. G. O. Alvim D. L. J. Pinheiro, V. H. Carvalho-Silva, M. Fioramonte, F. C. Gozzo, W. A. da Silva, G. W. Amarante, B. A. D. Neto, J. Org. Chem., 2018, 83, 12143-12153.

DOI: 10.1021/acs.joc.8b02101 (free Supporting Information)

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Abstract

Chiral task-specific ionic liquids bearing chiral anions as the catalysts enable an enantioselective multicomponent Biginelli reaction. A combined role of asymmetric counteranion-directed catalysis (ACDC) and ionic liquid effect (ILE) for the chiral induction in the Biginelli multicomponent reaction is demonstrated.

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proposed mechanism

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Key Words

Biginelli reaction, multicomponent reactions, organocatalysis

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ID: J42-Y2018