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Updated: Jan 16, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Remote asymmetric conjugate addition of naphthoquinone methides: constructing adjacent tertiary-quaternary carbon
Jing-Jing Zhai1, Shao-Jie Lou1, Xiao-Xiao Zhang1
1State Key Laboratory of Green Chemical Synthesis and Conversion, Key Laboratory of Green Pesticides and Cleaner Production Technology of Zhejiang Province, Catalytic Hydrogenation Research Center, Zhejiang University of Technology, Hangzhou 310014, P. R. China. wangyifeng@zjut.edu.cn.
Abstract:
The asymmetric reactions of naphthoquinone methides having carbonyl and methide units on different rings have remained underdeveloped due to the challenging remote stereoselectivity control. Herein, the asymmetric conjugate addition of in situ-generated naphthoquinone methides to β-ketoesters has been developed, in the presence of a chiral bis(oxazoline)-Cu(II) complex, providing various naphthol skeletons bearing adjacent tertiary-quaternary carbon stereocenters in high yields and enantioselectivities.
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