3,3'-bimorpholine derivatives as a new class of organocatalysts for asymmetric Michael addition.
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]
Mossé
Sarah
S
Department of Organic Chemistry, University of Geneva, 30 quai Ernest Ansermet, CH-1211 Geneva 4, Switzerland.
Laars
Marju
M
Kriis
Kadri
K
Kanger
Tõnis
T
Alexakis
Alexandre
A
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
D000447:Aldehydes; D000475:Alkenes; D009025:Morpholines; D009574:Nitro Compounds; D014753:Vinyl Compounds