Highly Enantioselective Catalytic Alkynylation of Quinolones: Substrate Scope, Mechanistic Studies, and Applications in the Syntheses of Chiral N-Heterocyclic Alkaloids and Diamines
ACS Catalysis2023Vol. 13(11), pp. 7661–7668
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Yong Guan, Tadas A. Buivydas, Rémy F. Lalisse, Kalen Laybourn, Charlotte L. Stern, Margaret Richins, Sean M. Burns, Arielle Shelby, Christopher M. Hadad, Anita E. Mattson
Abstract
The alkynylation of 4-siloxyquinolinium triflates has been achieved under the influence of copper bis(oxazoline) catalysis. The identification of the optimal bis(oxazoline) ligand was informed through a computational approach that enabled the dihydroquinoline products to be produced with up to 96% enantiomeric excess. The conversions of the dihydroquinoline products to biologically relevant and diverse targets are reported.
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