title: First asymmetric hetero Diels-Alder reaction of 1-sulfinyl dienes with nitroso derivatives. A new entry to the synthesis of optically pure 1,4-imino-L-ribitol derivatives.
abstract: Hetero Diels-Alder (HDA) cycloaddition of chiral 1-p-tolylsulfinyl-1,3-pentadiene with benzyl nitrosoformate, under mild conditions, yields 2H-1,2-oxazine 3 with complete regioselectivity and pi-facial diastereoselectivity. Sequential osmylation and protection of the resulting glycol gives the oxazine 5 which is directly transformed into enantiomerically pure 1,4,5-trideoxy-1,4-imino-L-ribitol 8 by reduction under Pd/C.
authors.affiliation: Departamento de Química Orgánica (E.T.S.I.I.), Universidad de Valladolid, Paseo del Cauce s/n, 47011, Valladolid, Spain.
authors.forename: C
authors.initials: C
authors.lastname: Arribas
authors.forename: M C
authors.initials: MC
authors.lastname: Carreño
authors.forename: J L
authors.initials: JL
authors.lastname: García-Ruano
authors.forename: J F
authors.initials: JF
authors.lastname: Rodríguez
authors.forename: M
authors.initials: M
authors.lastname: Santos
authors.forename: M A
authors.initials: MA
authors.lastname: Sanz-Tejedor
mesh_terms: D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009603:Nitroso Compounds / Q000737:chemistry*; D012255:Ribitol / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D009603:Nitroso Compounds; D012255:Ribitol; D006026:Glycoside Hydrolases