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Published on: May 26, 2019
Iron-Catalyzed Diastereoselective Intramolecular Olefin Aminobromination with Bromide Ion
Jun-Shan Tian1, Cheng-Liang Zhu1, Yun-Rong Chen1
1Department of Chemistry, Georgia State University, 100 Piedmont Avenue SE, Atlanta, GA 30303, USA.
Abstract:
A new iron-catalyzed diastereoselective aminobromination method is reported for both internal and terminal olefins (yield up to 90% and dr up to >20:1). In this transformation, a functionalized hydroxylamine and bromide ion were used as the nitrogen and bromine source, respectively. This method is compatible with a broad range of olefins and provides a convenient approach to synthetically valuable vicinal bromo primary amines. Our studies suggest that both the diastereoselectivity and enantioselectivity for the olefin aminobromination can be controlled by iron catalysts.
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