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Copper-catalysed selective hydroamination reactions of alkynes

Author(s)
Shi, Shi-Liang; Buchwald, Stephen Leffler
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Abstract
The development of selective reactions that utilize easily available and abundant precursors for the efficient synthesis of amines is a long-standing goal of chemical research. Despite the centrality of amines in a number of important research areas, including medicinal chemistry, total synthesis and materials science, a general, selective and step-efficient synthesis of amines is still needed. Here, we describe a set of mild catalytic conditions utilizing a single copper-based catalyst that enables the direct preparation of three distinct and important amine classes (enamines, α-chiral branched alkylamines and linear alkylamines) from readily available alkyne starting materials with high levels of chemo-, regio- and stereoselectivity. This methodology was applied to the asymmetric synthesis of ​rivastigmine and the formal synthesis of several other pharmaceutical agents, including ​duloxetine, ​atomoxetine, ​fluoxetine and ​tolterodine.
Date issued
2014-12
URI
http://hdl.handle.net/1721.1/99672
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Nature Chemistry
Publisher
Nature Publishing Group
Citation
Shi, Shi-Liang, and Stephen L. Buchwald. “Copper-Catalysed Selective Hydroamination Reactions of Alkynes.” Nature Chem 7, no. 1 (December 15, 2014): 38–44.
Version: Author's final manuscript
ISSN
1755-4330
1755-4349

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