Efficient synthesis of fumaric amides through cross-metathesis of acrylic amides with the NHC Grubbs ruthenium catalyst |
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| Institution: | 1. Department of Chemistry, Fuzhou University, Fuzhou 350108, People''s Republic of China;2. State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People''s Republic of China;1. Key Laboratory of Biology and Genetic Resources of Tropical Crops, Ministry of Agriculture, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, PR China;2. College of Pharmacy and Chemistry, Dali University, Dali 671000, PR China;1. Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, PR China;2. College of Life Science, Sichuan University, Chengdu 610064, PR China;3. Wenzhou University, Wenzhou 325035, PR China;1. Ecole Normale Supérieure, Departement de Chimie, UMR 7203 CNRS-UPMC-ENS, 24, rue Lhomond, 75005 Paris, France;2. Padua University – Department of Chemical Sciences, Via Marzolo 1, 35131 Padua, Italy;1. Department of Chemical Engineering & Applied Chemistry, University of Toronto, 200 College St., Toronto, Ontario M5S 3E5, Canada;2. Department of Chemical Engineering, Wuhan University of Science and Technology, 947 Heping Avenue, Wuhan, Hubei 430081, China;1. Key Laboratory of Strongly-Coupled Quantum Matter Physics, Chinese Academy of Sciences, University of Science and Technology of China, Hefei 230026, China;2. School of Physics and Electronic Engineering, Anqing Normal University, Anqing 246011, China |
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| Abstract: | Application of the second generation Grubbs metathesis catalyst for the homo-cross-metathesis of acroyl amides from chiral amines is reported. This efficient and high-yielding reaction provides a side-product free synthesis of fumaric acid diamides which are formed with complete (E)-selectivity under the reaction conditions. In particular, products which cannot be synthesized from the corresponding fumaroyl chloride via classic condensation route can now be provided in excellent yields (88–98%) with a catalyst loading from 2.5 mol% to even 0.375 mol%. |
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