Assembly of Fluorinated Quaternary Stereogenic Centers through Catalytic Enantioselective Detrifluoroacetylative Aldol Reactions

Abstract

A Cu-catalyzed asymmetric detrifluoroacetylative aldol addition reaction of 2-fluoro-1,3-diketones/hydrates to aldehydes in the presence of base and chiral bidentate ligand was developed. The reaction was carried out under convenient conditions and tolerated a wide range of substrates, resulting in fluorinated quaternary stereogenic α-fluoro-β-hydroxy ketone products with good chemical yields, diastereo- and enantioselectivities. This catalytic asymmetric detrifluoroacetylative aldol addition reaction provides a new approach for the preparation of biologically relevant products containing C-F quaternary stereogenic centers.

Keywords: CC bond cleavage; aldol reaction; asymmetric catalysis; detrifluoroacetylation; fluorinated quaternary stereocenters.