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Diastereoselective rhodium-catalyzed nitrene transfer starting from chiral sulfonimidamide-derived iminoiodanes
Institution:1. Department of Organic Chemistry and Laboratory of X-Ray Crystallography, University of Geneva, 30 quai Ernest Ansermet, CH-1211 Geneva 4, Switzerland;2. Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France;1. The Arnold and Mabel Beckman Laboratory for Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA;2. Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V. (IfOK), Buchbinderstraße 5-6, D-18055, Rostock, Germany;1. Department of Chemistry and Chemical Engineering, Jining University, Qufu 273155, China;2. School of Chemistry and Chemical Engineering, and Chongqing Key Laboratory of Theoretical and Computational Chemistry, Chongqing University, Chongqing 400030, China;3. College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, China;4. State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian 350002, China;1. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China;2. University of Chinese Academy of Sciences, Beijing 100049, China;3. Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Science, Chengdu, Sichuan 610041, China;1. Department of Medicinal Chemistry, BMC, Uppsala University, Box 574, SE-75123, Uppsala, Sweden;2. Department of Cell and Molecular Biology, BMC, Uppsala University, Box 596, SE-75123, Uppsala, Sweden;3. Department of Medical Biochemistry and Microbiology, BMC, Box 582, SE-75123, Uppsala, Sweden;4. Uppsala University, Science for Life Laboratory, Department of Cell and Molecular Biology, Box 596, SE-751 24, Uppsala, Sweden
Abstract:The dirhodium-catalyzed aziridination of olefins with chiral sulfonimidamides as iminoiodane precursors has been investigated under stoichiometric conditions. Diastereoisomeric excesses of up to 82% have been achieved using Rh2{(S)-nttl}4] as catalyst. Matching and mismatching effects were observed upon use of chiral rhodium(II) carboxylate catalysts.
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