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Oxidative Enantioselective α‐Fluorination of Aliphatic Aldehydes Enabled by N‐Heterocyclic Carbene Catalysis
Author(s) -
Li Fangyi,
Wu Zijun,
Wang Jian
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201409473
Subject(s) - enantioselective synthesis , carbene , chemistry , catalysis , oxidative phosphorylation , organocatalysis , organic chemistry , combinatorial chemistry , biochemistry
Described is the first study on oxidative enantioselective α‐fluorination of simple aliphatic aldehydes enabled by N‐heterocyclic carbene catalysis. N‐fluorobis(phenyl)sulfonimide serves as a an oxidant and as an “F” source. The CF bond formation occurs directly at the α position of simple aliphatic aldehydes, thus overcoming nontrivial challenges, such as competitive difluorination and nonfluorination, and proceeds with high to excellent enantioselectivities.