Asymmetric Construction of Carbon–Fluorine Quaternary Stereogenic Centers via Synergistic Pd/Cu Catalysis

We developed an asymmetric decarboxylative allylic alkylation of vinylethylene carbonates with α-fluoro pyridinyl acetates through a synergistic palladium/copper catalysis. This protocol provides chiral allylic alcohol with carbon–fluorine quaternary stereogenic centers in good yield with good enant...

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Bibliographic Details
Published in:Organic letters 2024-02, Vol.26 (6), p.1201-1206
Main Authors: Ke, Miaolin, Li, Xinzhi, Zong, Jiayi, Wang, Bowen, Zheng, Jinying, Zhang, Shujia, Chen, Jian-Ai, Chen, Fener
Format: Article
Language:English
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Summary:We developed an asymmetric decarboxylative allylic alkylation of vinylethylene carbonates with α-fluoro pyridinyl acetates through a synergistic palladium/copper catalysis. This protocol provides chiral allylic alcohol with carbon–fluorine quaternary stereogenic centers in good yield with good enantioselectivities and excellent regioselectivities. The utility of this approach was further demonstrated via a gram-scale experiment and derivatizations of the product.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c04375