Lewis Acid Catalyzed Asymmetric Three-Component Coupling Reaction: Facile Synthesis of α-Fluoromethylated Tertiary Alcohols.
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.
Department of Applied Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8552 (Japan), Fax: (+81) 3-5734-2776.
Kohsuke
K
Aikawa
Department of Applied Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8552 (Japan), Fax: (+81) 3-5734-2776.
Daisuke
D
Kondo
Department of Applied Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8552 (Japan), Fax: (+81) 3-5734-2776.
Kazuya
K
Honda
Department of Applied Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8552 (Japan), Fax: (+81) 3-5734-2776. mikami.k.ab@m.titech.ac.jp.
Koichi
K
Mikami
Lewis acids; alkynylation; fluorinated alcohols; palladium; three-component reaction