Chiral Squaramide‐Catalyzed Asymmetric Mannich Reactions for Synthesis of Fluorinated 3,3′‐Bisoxindoles

• Published in: Advanced synthesis & catalysis Vol. 360; no. 16; pp. 3164 - 3170
• Main Authors: Li, Bing‐Yu, Du, Da‐Ming
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 17.08.2018; Wiley Subscription Services, Inc
• Subjects: Asymmetric catalysis; Bisoxindoles; Chemical reactions; Chemical synthesis; Chemistry; Chemistry, Applied; Chemistry, Organic; Fluorination; Imines; Mannich addition; Organocatalysis; Physical Sciences; Science & Technology; Squaramides; Stereoselectivity; 3,3-DISUBSTITUTED OXINDOLES; VINYL SULFONE; ACIDS; REACTIVITY; 3-HALOOXINDOLES; Asymmetric catalysis; Organocatalysis; MEDICINAL CHEMISTRY; 3-FLUOROOXINDOLES; EFFICIENT ACCESS; Mannich addition; ENANTIOSELECTIVE CONJUGATE ADDITION; CONSTRUCTION; Squaramides; Bisoxindoles

A squaramide‐catalyzed asymmetric Mannich reaction of 3‐fluorooxindoles to isatin‐derived imines for synthesis of fluorinated 3,3′‐bisoxindoles with two contiguous stereocenters under mild conditions was developed. The corresponding 3,3′‐bisoxindoles were obtained in excellent yields with excellent...