Direct asymmetric Michael addition to nitroalkenes: vinylogous nucleophilicity under dinuclear zinc catalysis.
Under dinuclear catalysis, the direct conjugate addition of 2(5H)-furanone to nitroalkenes involves the gamma-position of the nucleophile. The synthetically versatile Michael adducts are prepared in good yields, with high levels of diastereo- and enantioselectivity. A model is presented to rationalize the observed stereoselectivity.
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.
Hitce
Julien
J
D015107:4-Butyrolactone / Q000138:chemical synthesis / Q000737:chemistry*; D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D000475:Alkenes; D007783:Lactones; D009574:Nitro Compounds; D015032:Zinc; D015107:4-Butyrolactone