Copper-Catalyzed Asymmetric Oxidative Desymmetrization of 2-Substituted 1,2,3-Triols

Asymmetric oxidative desymmetrization of 2-substituted glycerols has been achieved by using a new chiralbisoxazoline ligand/copper catalyst system with 1,3-dibromo-5,5-dimethylhydantoin and MeOH. The present transformationsmoothly proceeds with readily accessible 2-(hetero)aryl- and alkyl-substituted glycerols and provides straightforward access towardvarious glycerate derivatives in good to high yields with high enantioselectivities. The synthetic utility of the present protocol wasdemonstrated by the transformation of the optically active glycerol into a glyceraldehyde derivative

Automated summary

In this study, asymmetric oxidative desymmetrization of 2-substituted glycerols was achieved using a new chiral bisoxazoline ligand/copper catalyst system. The reaction smoothly proceeds with readily accessible 2-(hetero)aryl- and alkyl-substituted glycerols, providing various glycerate derivatives in good to high yields and high enantioselectivities. The synthetic utility of this protocol was demonstrated by transforming the optically active glycerol into a glyceraldehyde derivative.