Organocatalytic Enantioselective Michael Addition of 3‐Indolinone‐2‐Carboxylates to Maleimides. Issue 11 (22nd March 2018)

• Record Type: Journal Article
• Authors: Yarlagadda, Suresh; Reddy, C. Ravikumar; Ramesh, Boora; Kumar, G. Ravi; Sridhar, B.; Reddy, B. V. Subba
• Is Part Of: European journal of organic chemistry. Issue 11(2018)
• Page Start: 1364
• Page End: 1371
• Publication Date: 2018-03-22
• Subjects: Asymmetric catalysis -- Michael addition -- Nitrogen heterocycles -- Organocatalysis -- Enantioselectivity; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701670
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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, product4l was successfully converted into a chiral indoline‐pyrrolidine adduct. Abstract : 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.