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Updated: Mar 28, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Gold-catalyzed construction of two adjacent quaternary stereocenters via sequential C-H functionalization and aldol
Zhunzhun Yu1, Haile Qiu1, Lu Liu1
1Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, China. lliu@chem.ecnu.edu.cn jlzhang@chem.ecnu.edu.cn.
Abstract:
Herein, a novel and efficient gold-catalyzed intermolecular C(sp(2))-H functionalization (Friedel-Crafts alkylation) and aldol annulation strategy is presented. This cascade process allows the synthesis of a series of indanol and tetrahydronaphthalenol derivatives with two adjacent quaternary stereocenters. The attractive reaction features are the use of readily available starting materials, good diastereoselectivity, good functional-group tolerance and mild reaction conditions. Furthermore, preliminary results indicate that this transformation is amenable to enantioselectivitive synthesis with further chiral ligand screening and design.
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