Biomimetic Asymmetric 1,3-Dioplar Cycloaddition: Amino Acid Precursors in Biosynthesis Serve as Latent Azomethine Ylides

The first asymmetric catalytic biomimetic three-component 1,3-dipolar cycloaddition of alpha-keto esters and benzylamine with electron-deficient olefins, inspired by the transamination of a-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.