Anti-Markovnikov Hydroamination of Homoallylic Amines

Seth C. Ensign, Evan P. Vanable, Gregory D. Kortman, Lee J. Weir, Kami L. Hull

Research output: Contribution to journalArticle

Abstract

The development of an anti-Markovnikov-selective hydroamination of unactivated alkenes is a significant challenge in organometallic chemistry. Herein, we present the rhodium-catalyzed anti-Markovnikov-selective hydroamination of homoallylic amines. The proximal Lewis basic amine serves to promote reactivity and enforce regioselectivity through the formation of the favored metallacycle, thus over-riding the inherent reactivity of the alkene. The scope of both the amine nucleophiles and homoallylic amines that participate in the reaction is demonstrated.

Original languageEnglish (US)
Pages (from-to)13748-13751
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number43
DOIs
StatePublished - Nov 4 2015

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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  • Cite this

    Ensign, S. C., Vanable, E. P., Kortman, G. D., Weir, L. J., & Hull, K. L. (2015). Anti-Markovnikov Hydroamination of Homoallylic Amines. Journal of the American Chemical Society, 137(43), 13748-13751. https://doi.org/10.1021/jacs.5b08500