Biomimetic asymmetric 1,3-dioplar cycloaddition: Amino acid precursors in biosynthesis serve as latent azomethine ylides

Article abstract of DOI:10.1021/ol400983j

The first asymmetric catalytic biomimetic three-component 1,3-dipolar cycloaddition of α-keto esters and benzylamine with electron-deficient olefins, inspired by the transamination of α-keto acids involving pyridoxal phosphate (PLP)-dependent enzymes in biological systems, giving several families of structurally diverse pyrrolidine derivatives in high yields and excellent enantioselectivities (up to 99% ee) under mild conditions is described.