title: Short, highly efficient syntheses of protected 3-azido- and 4-azidoproline and their precursors.
abstract: [structure: see text] An improved synthesis of protected cis- and trans-3-azido-L-proline and cis- and trans-4-azido-L- and -D-proline is reported. These compounds have been synthesized from the corresponding hydroxyproline precursors using diphenylphosphoryl azide under Mitsunobu conditions. Short, highly efficient syntheses of these precursors are described, based on a new lactone-opening reaction and p-nitrobenzoate hydrolysis under very mild conditions.
authors.affiliation: Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208-3113, USA.
authors.forename: J A
authors.initials: JA
authors.lastname: Gómez-Vidal
authors.forename: R B
authors.initials: RB
authors.lastname: Silverman
mesh_terms: D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry; D006868:Hydrolysis; D006909:Hydroxyproline / Q000737:chemistry; D007202:Indicators and Reagents; D007783:Lactones / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: C434307:3-azidoproline; C434308:4-azidoproline; D001386:Azides; D007202:Indicators and Reagents; D007783:Lactones; D011392:Proline; D006909:Hydroxyproline