Enantioselective Synthesis of Succinimides by Michael Addition of 1,3-Dicarbonyl Compounds to Maleimides Catalyzed by a Chiral Bis(2-aminobenzimidazole) Organocatalyst

• Published in: European Journal of Organic Chemistry
• Main Authors: Gómez Torres, Eduardo, Alonso, Diego A., Gómez Bengoa, Enrique, Nájera, Carmen
• Other Authors: Universidad de Alicante. Departamento de Química Orgánica, Universidad de Alicante. Instituto Universitario de Síntesis Orgánica, Catálisis Estereoselectiva en Síntesis Orgánica (CESO), Síntesis Asimétrica (SINTAS)
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley-VCH Verlag GmbH & Co. KGaA 2013
• Subjects: Asymmetric catalysis; Organo­catalysis; Michael addition; Hydrogen bonds; Transition states; Química Orgánica; Orca
• Online Access: http://hdl.handle.net/10045/38278; https://doi.org/10.1002/ejoc.201201046

A wide variety of chiral succinimides have been prepared in high yields and enantioselectivities by asymmetric conjugate addition of 1,3-dicarbonyl compounds to maleimides under very mild reaction conditions using a bifunctional benzimidazole-derived organocatalyst. Computational and NMR studies support the hydrogen-bonding activation role of the catalyst and the origin of the stereoselectivity of the process. Financial support from the Ministerio de Educación y Ciencia (MEC) (project numbers CTQ2007-62771/BQU, CTQ2010-20387), from Consolider INGENIO 2010 (grant number CSD2007-00006), from the Generalitat Valenciana (PROMETEO/2009/038), from Fondos Europeos para el Desarrollo Regional (FEDER), from the University of Alicante, and from the European Union (EU) (ORCA Action CM0905) is acknowledged.