title: Chiral iminoesters derived from D-glyceraldehyde in [3 + 2] cycloaddition reactions. Asymmetric synthesis of a key intermediate in the synthesis of neuramidinase inhibitors.
abstract: Silver-catalyzed endo-selective and copper-catalyzed exo-selective asymmetric [3 + 2] cycloadditions of acrylates to chiral iminoesters derived from D-glyceraldehyde have been investigated. The reaction diastereoselectively provides highly functionalized pyrrolidines. This approach was used to develop the first asymmetric synthesis of a key intermediate in the synthesis of pyrrolidine influenza neuramidinase inhibitors.
authors.affiliation: Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC - Universidad de Zaragoza , Departamento de Catálisis y Procesos Catalíticos, Pedro Cerbuna 12, E-50009 Zaragoza, Spain.
authors.forename: José A
authors.initials: JA
authors.lastname: Gálvez
authors.forename: María D
authors.initials: MD
authors.lastname: Díaz-de-Villegas
authors.forename: Miriam
authors.initials: M
authors.lastname: Alías
authors.forename: Ramón
authors.initials: R
authors.lastname: Badorrey
mesh_terms: D003500:Cyclization; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D005985:Glyceraldehyde / Q000737:chemistry*; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D009439:Neuraminidase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D009975:Orthomyxoviridae / Q000201:enzymology*; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D004791:Enzyme Inhibitors; D004952:Esters; D007097:Imines; D011759:Pyrrolidines; D005985:Glyceraldehyde; D009439:Neuraminidase