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

Xu Han | Zendy; Quentin Gaignard Gaillard | Zendy; Pascal Retailleau | Zendy; Vincent Gandon | Zendy; Arnaud Voituriez | Zendy

Open Access

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

Author(s) -

Xu Han,

Quentin Gaignard Gaillard,

Pascal Retailleau,

Vincent Gandon,

Arnaud Voituriez

Publication year - 2022

Publication title -

chemical communications

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.837

H-Index - 333

eISSN - 1364-548X

pISSN - 1359-7345

DOI - 10.1039/d1cc06388j

Subject(s) - cycloisomerization , intramolecular force , enyne , chemistry , catalysis , nucleophile , indole test , reactivity (psychology) , enantioselective synthesis , stereochemistry , nucleophilic addition , medicinal chemistry , combinatorial chemistry , organic chemistry , medicine , alternative medicine , pathology

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.

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