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Enantioselective Synthesis of Succinimides by Michael Addition of 1,3‐Dicarbonyl Compounds to Maleimides Catalyzed by a Chiral Bis(2‐aminobenzimidazole) Organocatalyst
Author(s) -
GómezTorres Eduardo,
Alonso Diego A.,
GómezBengoa Enrique,
Nájera Carmen
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201046
Subject(s) - succinimides , chemistry , enantioselective synthesis , bifunctional , michael reaction , catalysis , conjugate , organic chemistry , organocatalysis , benzimidazole , stereoselectivity , squaramide , mathematical analysis , mathematics
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.