Synthesis of chiral polycyclic N-heterocycles via gold(i)-catalyzed 1,6-enyne cyclization/intramolecular nucleophilic addition?

Chemical Communications Pub Date: 2022-01-25 DOI: 10.1039/D1CC06388J

Abstract

Cycloisomerization of N-tethered indole- and dihydropyrrole-arylpropargyl substrates into complex polycycles was investigated by using gold(I) catalysis. Enantioselectivities up to 93% ee were obtained in the asymmetric version of this process. DFT calculations rationalized the reactivity observed for the formation of such complex molecular frameworks.

Graphical abstract: Synthesis of chiral polycyclic N-heterocycles via gold(i)-catalyzed 1,6-enyne cyclization/intramolecular nucleophilic addition
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