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. Author manuscript; available in PMC: 2021 Apr 15.
Published in final edited form as: J Am Chem Soc. 2020 Sep 11;142(38):16493–16505. doi: 10.1021/jacs.0c08599

Figure 1. Representative bioactive compounds containing N-propargylamines and the synthesis strategy to be pursued.

Figure 1.

(a) Examples of pharmaceutical agents that contain a propargylamine unit. (b) Enantioselective organocopper-catalyzed transformation of an α-amino C–H bond of tetrahydroisoquinolines into C–alkyne bond under oxidative conditions. (c) Coupling of N-alkylamines with trimethylsilylacetylenes by cooperative Lewis acid/Lewis acid catalysis. A possible mechanism might involve enantioselective C–C bond formation between an iminium ion and a chiral alkynylcopper complex via reactive intermediates that are generated in situ by cooperative functions of a chiral and an achiral Lewis acid co-catalyst.