Synthesis 2015; 47(12): 1709-1715
DOI: 10.1055/s-0034-1378719
© Georg Thieme Verlag Stuttgart · New York

Iron-Catalyzed Diastereoselective Intramolecular Olefin Aminobromination with Bromide Ion

Jun-Shan Tian
Cheng-Liang Zhu
Yun-Rong Chen
Hao Xu*
Further Information

Publication History

Received: 06 April 2015

Accepted after revision: 12 May 2015

Publication Date:
27 May 2015 (online)


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.

Supporting Information

  • References

  • 1 These authors contributed equally to this work.

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