The regiochemistry of reduction of mono-ethyl fumarate and maleate using a ruthenium BINAP catalyst |
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| Affiliation: | 1. Department of Chemistry, University of Missouri-St. Louis, St. Louis MO 63121, USA;2. Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor St., Chicago, IL 60607-7061, USA;1. Department of Chemistry, Government College University Faisalabad, 38000, Faisalabad, Pakistan;2. Department of Zoology, Government College University Faisalabad, 38000, Faisalabad, Pakistan;3. Department of Chemistry, University of Engineering and Technology Lahore, Faisalabad Campus, 38000, Faisalabad, Pakistan;4. Department of Chemistry, King Khalid University, Abha, 61413, P.O. Box 9004, Saudi Arabia;1. School of Mechanical Engineering, Chonnam National University, 77 Yongbong-ro, Buk-gu, Gwangju 61186, Republic of Korea;2. Department of Orthopedics, Chonnam National University Hwasun Hospital, 113 Ilsim-ri, Hwasun-eup, Hwasun-gun, Jeonnam 519-809, Republic of Korea;3. INM-Leibniz Institute for New Materials, Campus D2 2, Saarbrücken 66123, Germany;4. Institute of Fundamental and Frontier Sciences, University of Electronic Science and Technology of China, Chengdu, Sichuan 610054, China;1. State Key Laboratory of Bioelectronics, Jiangsu Key Laboratory for Biomaterials and Devices, School of Biological Science and Medical Engineering, Southeast University, Nanjing 210096, PR China;2. Department of Pharmaceutics, China Pharmaceutical University, Nanjing 210009, PR China;3. Jiangsu Key Laboratory of Molecular and Functional Imaging, Medical School, Southeast University, Nanjing 210009, PR China |
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| Abstract: | The regiochemistry of the reduction of mono-ethyl fumarate using bis(carboxylato){2,2′-bis(diphenylphosphino)-[R]-1,1-binapthyl}-ruthenium(II) (Ru[BINAP]) in H2/CH3OD is reported and occurs opposite to the regiochemistry observed in the reduction of tiglic acid. Reduction of mono-ethyl maleate with D2/CH3OD is very sluggish but produces meso-dideuteriosuccinic acid with high stereoselectivity. Reduction of mono-ethyl maleate with Ru[BINAP](O2CR)2 and H2/CH3OD results in mono-ethyl succinate-d1 with nearly complete loss of regiochemistry. |
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