Oxidative Intramolecular Bromo-Amination of N-Alkenyl Sulfonamides via Umpolung of Alkali Metal Bromides
Katsuhiko Moriyama*, Yuta Izumisawa and Hideo Togo*
*Department of Chemistry, Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan, Email: moriyamafaculty.chiba-u.jp, togofaculty.chiba-u.jp
K. Moriyama, Y. Izumisawa, H. Togo, J. Org. Chem., 2011, 76, 7249-7255.
DOI: 10.1021/jo201113r (free Supporting Information)
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The oxidative intramolecular bromo-amination of various N-alkenyl sulfonamides and N-alkenoxyl sulfonamides via umpolung of alkali metal bromides occurred exo-selectively to generate pyrrolidines and isoxazolidines in high yields with good diastereoselectivities. This method provided the desired products with a low amount of organic waste.
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