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Organocatalytic Enantioselective Michael Addition of 3‐Indolinone‐2‐Carboxylates to Maleimides
Author(s) -
Yarlagadda Suresh,
Reddy C. Ravikumar,
Ramesh Boora,
Kumar G. Ravi,
Sridhar B.,
Reddy B. V. Subba
Publication year - 2018
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.201701670
Subject(s) - chemistry , enantioselective synthesis , squaramide , bifunctional , stereocenter , michael reaction , conjugate , organocatalysis , indoline , succinimide , pyrrolidine , vicinal , organic chemistry , combinatorial chemistry , stereochemistry , catalysis , mathematical analysis , mathematics
An organocatalyzed asymmetric conjugate addition of 2‐substituted 3‐indolinones to maleimides has been developed by using a chiral bifunctional squaramide derived from quinidine to promote the reaction. This method provides easy access to 3‐indolinone‐2‐carboxylate‐succinimide adducts in high yields with excellent diastero and entantioselectivities and is a useful approach for the construction of vicinal quaternary‐tertiary chiral centers. In addition, product 4l was successfully converted into a chiral indoline‐pyrrolidine adduct.