Visible Light-Promoted Enantioselective Aerobic Hydroxylation of β-Ketocarbonyls by Chiral Primary Amine Catalysis
Mao Cai, Kaini Xu, Haoyuan Jia, Long Zhang, Xueling Mi, Sanzhong Luo
Abstract
Highly effective and stereoselective enamine-singlet oxygen coupling was achieved by synergistic chiral primary amine and photocatalysis in hexafluoroisopropanol. The current enamine catalysis enables α -hydroxylation of β -ketocarbonyls with good yields and high enantioselectivity across a broad range of substrates. Mechanistic studies revealed a direct participation of solvents in the critical enamine coupling step, and a solvent- 1 O 2 H-bonding mode was invoked to account for the dramatic solvent effect.
Topics & Concepts
EnamineChemistryEnantioselective synthesisHydroxylationCatalysisSinglet oxygenAmine gas treatingOrganocatalysisSolventStereoselectivityPhotochemistryOrganic chemistryOxygenEnzymeOxidative Organic Chemistry ReactionsSynthesis and Catalytic ReactionsRadical Photochemical Reactions