title: Enantioselective direct vinylogous Michael addition of functionalized furanones to nitroalkenes catalyzed by an axially chiral guanidine base.
abstract: The highly syn-diastereo- and enantioselective direct vinylogous Michael addition of α-thio substituted furanones with conjugate nitroalkenes was demonstrated using an axially chiral guanidine base catalyst. The method provides facile access to enantioenriched α,γ-functionalized butenolides that can be further manipulated, thereby rendering them useful synthetic intermediates.
authors.affiliation: Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan. mterada@m.tohoku.ac.jp
authors.forename: Masahiro
authors.initials: M
authors.lastname: Terada
authors.forename: Kenichi
authors.initials: K
authors.lastname: Ando
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000737:chemistry*; D019791:Guanidine / Q000737:chemistry*; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000475:Alkenes; D005663:Furans; D009574:Nitro Compounds; D014753:Vinyl Compounds; D019791:Guanidine; C039281:furan