title: 3,3'-bimorpholine derivatives as a new class of organocatalysts for asymmetric Michael addition.
abstract: New N-alkyl-3,3'-bimorpholine derivatives (iPBM) were revealed to be efficient organocatalysts for the asymmetric direct Michael addition of aldehydes to nitroolefins and a vinyl sulfone. In these transformations using iPBM, 1,4-adducts were afforded in high yields, with good to high levels of diastereo- and enantioselectivity. The stereochemical outcome of the reaction could be explained by an acyclic synclinal model. [reaction: see text]
authors.affiliation: Department of Organic Chemistry, University of Geneva, 30 quai Ernest Ansermet, CH-1211 Geneva 4, Switzerland.
authors.forename: Sarah
authors.initials: S
authors.lastname: Mossé
authors.forename: Marju
authors.initials: M
authors.lastname: Laars
authors.forename: Kadri
authors.initials: K
authors.lastname: Kriis
authors.forename: Tõnis
authors.initials: T
authors.lastname: Kanger
authors.forename: Alexandre
authors.initials: A
authors.lastname: Alexakis
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D008958:Models, Molecular; D015394:Molecular Structure; D009025:Morpholines / Q000138:chemical synthesis / Q000737:chemistry*; D009574:Nitro Compounds / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000475:Alkenes; D009025:Morpholines; D009574:Nitro Compounds; D014753:Vinyl Compounds