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Chiral quinolinyl-oxazolines as ligands for copper(I)-catalyzed asymmetric cyclopropanation
Affiliation:1. Medical Imaging Key Laboratory of Sichuan Province and Affiliated Hospital of North Sichuan Medical College, North Sichuan Medical College, Nanchong 637000, P.R. China;2. State Key Laboratory of Elemento-Organic Chemistry and Tianjin Key Laboratory of Biosensing and Molecular Recognition, College of Chemistry, Nankai University, Tianjin 300071, P.R. China;3. Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, P.R. China;4. Haihe Laboratory of Sustainable Chemical Transformations, Tianjin 300192, P.R. China;1. Department of Chemistry, Gwangju Institute of Science and Technology (GIST), 123 Cheomdan-gwagiro, Buk-gu, Gwangju, 61005, Republic of Korea;2. Chiral Technology Korea (CTK), Biz Center C-620, 17, Techno 4-ro, Youseong-gu, Daejeon, 34013, Republic of Korea;3. School of Materials Science and Engineering, Gwangju Institute of Science and Technology, 123 Cheomdan-gwagiro, Buk-gu, Gwangju, 61005, Republic of Korea;1. Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Faculty of Chemistry, Northeast Normal University, Changchun 130024, PR China;2. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, PR China;1. Department of Chemistry, Zhejiang University, Hangzhou 310027, China;1. Institute for Research in Biomedicine (IRB Barcelona), The Barcelona Institute of Science and Technology (BIST), Baldiri Reixac 10, 08028 Barcelona, Spain;2. Departament de Química Inorgànica i Orgànica, Secció Orgànica, Facultat de Química, Universitat de Barcelona, Martí i Franqués 1, 08028 Barcelona, Spain
Abstract:
Chiral quinolinyl-oxazoline compounds have been synthesized from enantiomerically pure amino alcohols and 8-quinoline-carboxylic acid using a convenient procedure. Asymmetric cyclopropanation of styrene with diazoacetates in the presence of 1 mol% of CuOTf and quinolinyl-oxazolines gave 2-phenylcyclopropane carboxylates in moderate enantiomeric excesses.
Keywords:
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