title: Biomimetic asymmetric 1,3-dioplar cycloaddition: amino acid precursors in biosynthesis serve as latent azomethine ylides.
abstract: 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.
authors.affiliation: Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.
authors.forename: Chang
authors.initials: C
authors.lastname: Guo
authors.forename: Jin
authors.initials: J
authors.lastname: Song
authors.forename: Liu-Zhu
authors.initials: LZ
authors.lastname: Gong
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry* / Q000378:metabolism*; D001391:Azo Compounds / Q000737:chemistry*; D032701:Biomimetics; D061565:Cycloaddition Reaction; D004952:Esters / Q000737:chemistry*; D015394:Molecular Structure; D011498:Protein Precursors / Q000096:biosynthesis* / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000737:chemistry*
chemical_list: D000475:Alkenes; D000596:Amino Acids; D001391:Azo Compounds; D004952:Esters; D011498:Protein Precursors; D011759:Pyrrolidines; D013882:Thiosemicarbazones; C512188:azomethine