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Lewis Base Catalyzed Ring Opening of Aziridines with Silylated Nucleophiles

Satoshi Minakata, Yuriko Okada, Yoji Oderaotoshi and Mitsuo Komatsu*

*Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan, Email: komatsuchem.eng.osaka-u.ac.jp

S. Minakata, Y. Okada, Y. Oderaotoshi, M. Komatsu, Org. Lett., 2005, 7, 3509-3512.

DOI: 10.1021/ol051186f (free Supporting Information)


Abstract

β-Functionalized sulfonamides were produced in good yields by the regioselective ring opening of N-tosylaziridines with trimethylsilylated nucleophiles, catalyzed by N,N,N',N'-tetramethylethylenediamine (TMEDA).

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Key Words

Aziridines, 1,2-azidoamines, Iodides, Bromides, Nitriles


ID: J54-Y2005-1020