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Updated: Jan 9, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Tandem Desymmetric Condensation and Oxidative Cyclization to Construct Chiral 4-Carbonyl-quinoline Fused
Tao Huang1, Li-E Wang1, Wei-Hong Duan1
1Key Laboratory of Green Catalysis of Jiangxi Education Institutes, Jiangxi Normal University, Nanchang, Jiangxi 330022, China.
Abstract:
A catalytic desymmetric tandem carbonyl-amine condensation and oxidative cyclization reaction between 2-alkylaniline and prochiral 1,3-cyclobutadiones is developed to synthesize chiral 4-carbonyl-quinoline fused cyclobutanones bearing a quaternary carbon center in good to high yields with up to 94% ee values. This one-pot annulation sequence represents the first application of Cu-catalyzed oxidative cyclization of the N-(2-alkynylaryl)enamine intermediate to construct chiral polycyclic quinoline derivatives. Preliminary mechanistic studies supported the radical process nature of the oxidative cyclization step.
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