Organocatalytic Enantioselective Michael Addition of 3‐Indolinone‐2‐Carboxylates to Maleimides

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...

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Bibliographic Details
Published in:European journal of organic chemistry 2018-03, Vol.2018 (11), p.1364-1371
Main Authors: Yarlagadda, Suresh, Reddy, C. Ravikumar, Ramesh, Boora, Kumar, G. Ravi, Sridhar, B., Reddy, B. V. Subba
Format: Article
Language:English
Subjects:
Adducts
Asymmetric catalysis
Carboxylates
Enantioselectivity
Michael addition
Nitrogen heterocycles
Organocatalysis
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Summary: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. The asymmetric conjugate addition of 2‐substituted 3‐indolinones to maleimides has been achieved by using a chiral bifunctional squaramide as an organocatalyst. This method provides easy access to 3‐indolinone‐2‐carboxylate‐succinimide adducts in high yields with exellent diastereo‐ and enantioselectivities.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201701670