Lewis Acid Catalyzed Asymmetric Three‐Component Coupling Reaction: Facile Synthesis of α‐Fluoromethylated Tertiary Alcohols. Issue 49 (21st October 2015)

• Record Type: Journal Article
• Authors: Aikawa, Kohsuke; Kondo, Daisuke; Honda, Kazuya; Mikami, Koichi
• Is Part Of: Chemistry. Volume 21:Issue 49(2015)
• Page Start: 17565
• Page End: 17569
• Publication Date: 2015-10-21
• Subjects: alkynylation -- fluorinated alcohols -- Lewis acids -- palladium -- three‐component reaction; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201503631
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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. Abstract : Atom‐economical : The catalytic asymmetric three‐component coupling reaction using a chiral dicationic palladium complex as an efficient Lewis acid catalyst is shown to lead to the construction of valuable chiral organofluorine compounds. Moreover, this coupling reaction results in perfect regioselectivities and high enantioselectivities of the corresponding tertiary allylic alcohols in good to excellent yields.