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Enantiomeric resolution and determination of the absolute configuration of dibenzophosphole 5-oxides
Institution:1. Departament de Quı́mica Orgànica, Universitat de Barcelona, Martı́ i Franquès, 1-11, E-08028 Barcelona, Spain;2. Departament de Quı́mica Inorgànica, Universitat de Barcelona, Diagonal 647, E-08028 Barcelona, Spain;3. Departament de Cristallografia i Dipòsits Minerals, Universitat de Barcelona, Martı́ i Franquès s/n, E-08028 Barcelona, Spain;1. Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China;2. College of Chemistry and Chemical Engineering, Henan University, Kaifeng, Henan 475004, China;3. University of Chinese Academy of Sciences, Beijing 10049, China;1. Department of Nanomaterials Engineering, Chungnam National University, 79 Daehak-ro, Yuseong-gu, Daejeon 305-764, Republic of Korea;2. Graduate School of Energy Science and Technology, Chungnam National University, 79 Daehak-ro, Yuseong-gu, Daejeon 305-764, Republic of Korea;3. RASOM, Chungnam National University, 79 Daehak-ro, Yuseong-gu, Daejeon 305-764, Republic of Korea
Abstract:The resolution of asymmetrically substituted dibenzophospholes via chromatographic separation of their cyclopalladium derivatives is described for the first time. The absolute configuration of the phosphorus atom was determined by X-ray crystallographic analysis in one case. A general NMR criterion for the complete determination of the configuration of this group of products is proposed. The enantiomeric excess of the resolved compounds was determined by NMR Eu(III) chemical displacement experiments and by HPLC using a chiral stationary phase.
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