Copper-catalysed selective hydroamination reactions of alkynes
Name
Buchwald_Copper-catalysed.pdf
Size
645.89 KB
Format
Adobe PDF
Checksum (MD5)
44c6f48a8071edd3432b926539526b0b
Author(s)
Shi, Shi-Liang
Buchwald, Stephen Leffler
Date Issued
December 2014
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
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
Persistent DSpace Link
DOI of Published Version
https://doi.org/10.1038/nchem.2131
