title: Hydrogen-bond-mediated asymmetric cascade reaction of stable sulfur ylides with nitroolefins: scope, application and mechanism.
abstract: A hydrogen-bond-mediated asymmetric [4+1] annulation/rearrangement cascade of stable sulfur ylides and nitroolefins was developed. This reaction provides a facile route to enantioenriched 4,5-substituted oxazolidinones in moderate to excellent isolated yields (65-96 %) with excellent stereocontrol (up to more than 95:5 d.r. and 97:3 e.r.). This methodology was successfully applied to the concise synthesis of two bioactive molecules. The stereocontrolled modes and mechanism have been proposed to explain the origin of this stereochemistry.
authors.affiliation: Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, PR China.
authors.forename: Liang-Qiu
authors.initials: LQ
authors.lastname: Lu
authors.forename: Fang
authors.initials: F
authors.lastname: Li
authors.forename: Jing
authors.initials: J
authors.lastname: An
authors.forename: Ying
authors.initials: Y
authors.lastname: Cheng
authors.forename: Jia-Rong
authors.initials: JR
authors.lastname: Chen
authors.forename: Wen-Jing
authors.initials: WJ
authors.lastname: Xiao
mesh_terms: D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D006860:Hydrogen Bonding; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry
chemical_list: D000475:Alkenes; D009574:Nitro Compounds; D023303:Oxazolidinones; D013455:Sulfur