Work

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

Year: 2023

Type: article

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.

Source: ACS Catalysis

DOI: 10.1021/acscatal.3c01536

Authors: Yong Guan, Tadas A. Buivydas, Remy F. Lalisse, Kalen B. Laybourn, Charlotte Stern, Margaret Richins, Sean M. Burns, Arielle Shelby, Christopher M. Hadad, Anita E. Mattson

Institutions: Worcester Polytechnic Institute, The Ohio State University, Northwestern University, Emory University

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,000

Funders: National Science Foundation, National Institutes of Health, National Institute of General Medical Sciences

Awards: Silanediol Enabled Drug Discovery, NRT-HDR: Data-Driven Sustainable Engineering for a Circular Economy, REU Site: Membrane Biochemistry and Bioinspired Synthesis

OpenAlex ID: W4377824958

FWCI: 0.817

Cites: 46

Cited by: 8

Related to: 10