Highly Enantioselective Catalytic Alkynylation of Quinolones: Substrate Scope, Mechanistic Studies, and Applications in the Syntheses of Chiral N-Heterocyclic Alkaloids and Diamines

The alkynylationof 4-siloxyquinolinium triflates has been achievedunder the influence of copper bis-(oxazoline) catalysis. The identificationof the optimal bis-(oxazoline) ligand was informed through a computationalapproach that enabled the dihydroquinoline products to be producedwith up to 96% enantiomeric excess. The conversions of the dihydroquinolineproducts to biologically relevant and diverse targets are reported.

Automated summary

The alkynylation of 4-siloxyquinolinium triflates was successfully achieved using copper bis-(oxazoline) catalysis. The optimal bis-(oxazoline) ligand was identified through computational analysis, resulting in dihydroquinoline products with up to 96% enantiomeric excess. Conversion of the dihydroquinoline products to biologically relevant and diverse targets was reported.