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Lewis Acid Catalyzed Asymmetric Three‐Component Coupling Reaction: Facile Synthesis of α‐Fluoromethylated Tertiary Alcohols
Author(s) -
Aikawa Kohsuke,
Kondo Daisuke,
Honda Kazuya,
Mikami Koichi
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503631
Subject(s) - catalysis , allylic rearrangement , chemistry , lewis acids and bases , tertiary alcohols , alkyne , component (thermodynamics) , palladium , coupling reaction , coupling (piping) , organic chemistry , lewis acid catalysis , combinatorial chemistry , polymer chemistry , materials science , physics , metallurgy , thermodynamics
A chiral dicationic palladium complex is found to be an efficient Lewis acid catalyst for the synthesis of α‐fluoromethyl‐substituted tertiary alcohols using a three‐component coupling reaction. The reaction transforms three simple and readily available components (terminal alkyne, arene, and fluoromethylpyruvate) to valuable chiral organofluorine compounds. This strategy is completely atom‐economical and results in perfect regioselectivities and high enantioselectivities of the corresponding tertiary allylic alcohols in good to excellent yields.