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Enantioselective palladium-catalyzed C(sp2)-H carbamoylation
Institution:1. School of Physical Science and Technology, ShanghaiTech University, Shanghai 200031, China;2. State Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai, 200032, China;1. School of Science and Institute of Scientific Research, Great Bay University, Dongguan 523000, China;2. Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, China;3. Academy for Advanced Interdisciplinary Studies and Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China;1. Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520-8107, USA;2. Department of Pathology, Immunobiology, Comparative Medicine, Yale School of Medicine, 310 Cedar Street, New Haven, CT 06520, USA;3. College of Pharmaceutical Sciences, Zhejiang University, 866 Yuhangtang Rd, Hangzhou 310018, P. R. China;4. Department of Molecular Biophysics and Biochemistry, Yale University, New Haven, CT 06520, USA;1. Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, China;2. Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology, Shenzhen 518055, China;1. Department of Chemistry, South University of Science and Technology of China, Shenzhen 518055, China;2. College of Chemistry, Nankai University, Tianjin 300071, China;3. State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, China
Abstract:An enantioselective palladium-catalyzed C(sp2)-H carbamoylation for the preparation of chiral isoindolines was described for the first time. With chiral monophosphorus ligand (R)-AntPhos as the ligand, a series of chiral isoindolines were prepared from diarylmethyl carbamoyl chlorides in excellent yields and enantioselectivities with the palladium loading as low as 1 mol%. Initial mechanistic studies indicated the asymmetric cyclization catalyzed a palladium species with a single chiral monophosphorus ligand.
Keywords:Carbamoylation  Enantioselective  Isoindolines  Palladium catalysis  Chiral phosphorus ligand
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