Copper-catalysed selective hydroamination reactions of alkynes
Author(s)Shi, Shi-Liang; Buchwald, Stephen Leffler
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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.
DepartmentMassachusetts Institute of Technology. Department of Chemistry
Nature Publishing Group
Shi, Shi-Liang, and Stephen L. Buchwald. “Copper-Catalysed Selective Hydroamination Reactions of Alkynes.” Nature Chem 7, no. 1 (December 15, 2014): 38–44.
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