title: Enantioselective cascade reactions of stable sulfur ylides and nitroolefins through an axial-to-central chirality transfer strategy.
abstract: An enantioselective [4 + 1] annulation/rearrangement cascade of stable sulfur ylides and nitroolefins has been developed through an efficient axial-to-central chirality transfer with the use of a chiral BINOL-derived sulfide as a reliable stereocontroller. It can provide pharmaceutically and synthetically important oxazolidinones in high stereoselectivities (up to 96:4 e.r. and >95:5 d.r.). Moreover, this strategy was also successfully applied to the asymmetric [4 + 1]/[3 + 2] cycloaddition cascade of sulfur ylides with alkene-tethered nitroolefins, and the corresponding enantioenriched fused heterocycles (up to 87:13 e.r. and >95:5 d.r.) were obtained in good to excellent yields (54-95% yields).
authors.affiliation: Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, China.
authors.forename: Liang-Qiu
authors.initials: LQ
authors.lastname: Lu
authors.forename: Zhi-Hui
authors.initials: ZH
authors.lastname: Ming
authors.forename: Jing
authors.initials: J
authors.lastname: An
authors.forename: Chao
authors.initials: C
authors.lastname: Li
authors.forename: Jia-Rong
authors.initials: JR
authors.lastname: Chen
authors.forename: Wen-Jing
authors.initials: WJ
authors.lastname: Xiao
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry*
chemical_list: D000475:Alkenes; C406944:BINOL, naphthol; D009284:Naphthols; D009574:Nitro Compounds; D013455:Sulfur