An organocatalytic asymmetric Mannich reaction of pyrazoleamides with cyclic trifluoromethyl ketimines: enantioselective access to dihydroquinazolinone skeletons. Issue 18 (25th April 2018)

• Record Type: Journal Article
• Authors: Luo, Yuan; Xie, Ke-Xin; Yue, Deng-Feng; Zhang, Xiao-Mei; Xu, Xiao-Ying; Yuan, Wei-Cheng
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 18(2018)
• Page Start: 3372
• Page End: 3375
• Publication Date: 2018-04-25
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob00707a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A series of trifluoromethyl dihydroquinazolinones were obtained in excellent results via an asymmetric Mannich reaction of pyrazoleamides and cyclic trifluoromethyl ketimines. Abstract : An organocatalyzed asymmetric Mannich reaction of pyrazoleamides and cyclic trifluoromethyl ketimines with a chiral bifunctional amine-squaramide as the catalyst was developed. A wide range of trifluoromethyl dihydroquinazolinone derivatives bearing adjacent quaternary and tertiary stereogenic centers were readily obtained in good to excellent yields (up to 99%) with high diastereo- and enantioselectivities (up to 99% ee and >20 : 1 dr). The large scale experiment and transformation of the product have also been demonstrated.