title: Organocatalytic Asymmetric Benzylation and Aldol-Hemiacetalization of α,β-Unsaturated Trifluoromethyl Ketones: Efficient Enantioselective Construction of 3,4-Dihydroisocoumarins.
abstract: A new method has been developed for the organocatalytic enantioselective benzylation and aldol-hemiacetalization of α,β-unsaturated trifluoromethyl ketones with toluene derivatives in the presence of a tertiary amine-thiourea catalyst. This method represents a facile and efficient strategy for the asymmetric synthesis of optically active 3,4-dihydroisocoumarins bearing a trifluoromethylated tetrasubstituted carbon stereocenter with high enantioselectivity. Notably, this strategy was used to synthesize several chiral trifluoromethylated analogues of typharin with high efficiency.
authors: Department of Chemistry, South University of Science and Technology of China, 1088 Xueyuan Blvd., Nanshan District, Shenzhen, Guangdong, 518055, P. R. China.
authors: Jindian
authors: J
authors: Duan
authors: Department of Chemistry, South University of Science and Technology of China, 1088 Xueyuan Blvd., Nanshan District, Shenzhen, Guangdong, 518055, P. R. China.
authors: Yuyu
authors: Y
authors: Cheng
authors: Department of Chemistry, South University of Science and Technology of China, 1088 Xueyuan Blvd., Nanshan District, Shenzhen, Guangdong, 518055, P. R. China.
authors: Jing
authors: J
authors: Cheng
authors: Department of Chemistry, South University of Science and Technology of China, 1088 Xueyuan Blvd., Nanshan District, Shenzhen, Guangdong, 518055, P. R. China.
authors: Rou
authors: R
authors: Li
authors: Department of Chemistry, South University of Science and Technology of China, 1088 Xueyuan Blvd., Nanshan District, Shenzhen, Guangdong, 518055, P. R. China.
authors: Pengfei
authors: P
authors: Li
mesh_terms: D000447:Aldehydes; D000588:Amines / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D003374:Coumarins / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D049934:Isocoumarins / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry; D014050:Toluene / Q000031:analogs & derivatives
chemical_list: D000447:Aldehydes; D000588:Amines; D003374:Coumarins; D049934:Isocoumarins; D007659:Ketones; C473707:typharin; D014050:Toluene; D002244:Carbon; C116609:3-hydroxybutanal; C030123:coumarin; D013890:Thiourea
keywords: aldol; enone; isocoumarin; organocatalysis; trifluoromethyl