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

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Abstract

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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Key Words

Isoxazolidines, Oxone

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ID: J42-Y2011-2590