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Stereoselective Aminobromination of Alkylidenecyclopropanes with TsNH2 and NBS as Nitrogen and Bromine Sources: A Simple Access to γ-Bromohomoallylic Sulfonamides

Xian Huang*, Wei-Jun Fu

*Department of Chemistry, Zhejiang University (Campus Xixi), Hangzhou 310028, P. R. of China, Email: huangxmail.hz.zj.cn

X. Huang, W.-J. Fu, Synthesis, 2006, 1016-1017.

DOI: 10.1055/s-2006-926322

Abstract

A convenient and efficient method for aminobromination of alkylidenecyclopropanes is reported. This is exemplified in the stereoselective preparation of N-[(Z)-3-bromobut-3-en-1-yl]-p-toluenesulfonamides by using p-toluenesulfonamide and N-bromosuccinimide (NBS) as nitrogen and bromine sources, respectively.

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Key Words

aminobromination, vinyl bromides, alkylidenecyclopropanes, p-toluenesulfonamide, N-bromosuccinimide, homoallylic sulfonamide, homoallylic amines, stereoselective

ID: J66-Y2006-630