Screening of a modular sugar-based phosphite ligand library in the Cu-catalyzed asymmetric 1,4-addition reactions

Abstract

A sugar-based monophosphite ligand library L1– L5 was screened in the Cu-catalyzed asymmetric 1,4-addition to cyclic and aliphatic linear enones. These ligands are derived from d-glucose, d-galactose and d-fructose, which lead to a wide range of sugar backbones, and contain several substituents/configurations in the biaryl moiety, with different steric and electronic properties. Systematic variation of the ligand parameters indicates that the catalytic performance (activities and enantioselectivities) is highly affected by the configuration of C-4 of the carbohydrate backbone, the size of the ring of the sugar backbone and the cooperative effect between configurations of C-3 and of the binaphthyl phosphite moiety. Good activities and enantioselectivities up to 57% and 51% were achieved for cyclic and aliphatic linear enones, respectively.