Visible Light Catalyzed Asymmetric Radical Coupling Reaction Of Azaaryl Ketone And N-arylglycine

1,2-Aminoalcohol structures widely exist in pharmaceutical active molecules,natural products and some important ligands and catalysts.At present,the common methods for preparing chiral 1,2-amino alcohols include amino acid reduction method,ring-opening amination of epoxy compounds,Mannich-type reaction,bifunctionalization of olefins,etc.,and the method of photocatalytic free radical coupling has also been reported.Due to the high reactivity of free radicals and the low energy of hydrogen bonding interactions,the chirality control of free radical reactions has always been a difficult point in chemical synthesis.Synergistic catalysis of photosensitizers and chiral catalysts has become a general strategy for stereocontrol of such reactions.Photocatalysis has the characteristics of green,pollution-free and sustainable,and strong tolerance of functional groups,which has become a powerful synthetic tool in organic synthesis.We used the self-developed DPZ as the photocatalyst and chiral phosphoric acid(CPA)as the hydrogen bonding catalyst to synthesize a series of 1,2-amino alcohol compounds.In this reaction,the basic carbonyl group generates a neutral carbonyl radical,which interacts with the chiral phosphoric acid catalyst through hydrogen bonding,thereby realizing the steric control of the reaction.This method demonstrates the practical feasibility of the hydrogen-bonding catalysis strategy.