Highly Enantioselective Synthesis of 3 a -Fluorofuro[3,2- b ]indolines via Organocatalytic Aza-Friedel-Crafts Reaction/Selective C-F Bond Activation

Fluoroalkylated compounds are of high interest in drug discovery and have inspired the evolution of diverse C-F bond activation methodologies. However, the selective activation of polyfluorinated compounds remains challenging. Herein, we describe an unprecedented strategy for synthesizing enantioenr...

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Published in:Organic letters 2023-12, Vol.25 (48), p.8666-8671
Main Authors: Ma, Tao, Wei, Xing-Pin, Wang, Xin-Chun, Qiao, Xiu-Xiu, Li, Ganpeng, He, Yonghui, Zhao, Xiao-Jing
Format: Article
Language:English
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Summary:Fluoroalkylated compounds are of high interest in drug discovery and have inspired the evolution of diverse C-F bond activation methodologies. However, the selective activation of polyfluorinated compounds remains challenging. Herein, we describe an unprecedented strategy for synthesizing enantioenriched fluorofuro[3,2- ]indolines through the organocatalytic aza-Friedel-Crafts reaction coupled with selective C-F bond activation. These reactions feature excellent enantioselectivities (≤96% ee) and yields (≤96%) as well as good functional group compatibility. Mechanistic investigations by means of F nuclear magnetic resonance experiments provided sufficient support for silica gel as the key medium in this transformation.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03445