Enantioselective Synthesis of Succinimides by Michael Addition of 1,3-Dicarbonyl Compounds to Maleimides Catalyzed by a Chiral Bis(2-aminobenzimidazole) Organocatalyst
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 sup...
Published in: | European Journal of Organic Chemistry |
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Main Authors: | , , , |
Other Authors: | , , , |
Format: | Article in Journal/Newspaper |
Language: | English |
Published: |
Wiley-VCH Verlag GmbH & Co. KGaA
2013
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Subjects: | |
Online Access: | http://hdl.handle.net/10045/38278 https://doi.org/10.1002/ejoc.201201046 |
Summary: | 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. |
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