title: Efficient stereoselective nucleophilic addition of pyrroles to chiral nitrones.
abstract: Regioselective additions of pyrroles to a variety of optically active nitrones under smooth acidic conditions lead to chiral pyrrolic N-hydroxylamines in good to excellent yields. Depending on the position of the chirality on the nitrone partner, the addition products have been isolated with high diastereoselectivity levels. Reaction of glyoxylate based chiral nitrones either at the C-2 or at the C-3 position of the pyrrole nucleus afforded N-hydroxyamino esters in high yields as single diastereoisomers. These adducts allow access to enantio-enriched non proteinogenic 2'- and 3'-pyrrolylglycines (13 and 19 respectively).
authors.affiliation: Département de Chimie Moléculaire (SERCO) UMR-5250, ICMG FR-2607, Université Joseph Fourier, CNRS, BP-53, 38041, Grenoble Cedex 9, France.
authors.forename: Christophe
authors.initials: C
authors.lastname: Berini
authors.forename: Frédéric
authors.initials: F
authors.lastname: Minassian
authors.forename: Nadia
authors.initials: N
authors.lastname: Pelloux-Léon
authors.forename: Jean-Noël
authors.initials: JN
authors.lastname: Denis
authors.forename: Yannick
authors.initials: Y
authors.lastname: Vallée
authors.forename: Christian
authors.initials: C
authors.lastname: Philouze
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry; D009589:Nitrogen Oxides / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D011760:Pyrrolidinones / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000596:Amino Acids; D009589:Nitrogen Oxides; D011758:Pyrroles; D011760:Pyrrolidinones; C015388:nitrones; D009584:Nitrogen