Catalytic Enantioselective Synthesis of Chiral Organofluorine Compounds: Alcohol-Mediated Hydrogen Transfer for Catalytic Carbonyl Reductive Coupling

Org Process Res Dev. 2019;23(5):730-736. doi: 10.1021/acs.oprd.9b00035. Epub 2019 Mar 22.

Abstract

Alcohol-mediated carbonyl addition has enabled catalytic enantioselective syntheses of diverse fluorine-containing compounds without the need for stoichiometric metals or discrete redox manipulations. Reactions of this type may be separated into two broad categories: redox-neutral hydrogen auto-transfer reactions wherein lower alcohols and n-unsaturated pronucleophiles are converted to higher alcohols and corresponding 2-propanol mediated carbonyl reductive couplings.

Keywords: carbonyl addition; enantioselective catalysis; fluorine; hydrogen transfer; iridium; ruthenium.