M. A. Galkina, G. V. Bodrin, E. I. Goryunov, I. B. Goryunova, A. S. Sherstneva, J. S. Urmambetova, N. G. Kolotyrkina, M. M. Il'in, V. K. Brel, K. A. Kochetkov, “Regioselective aza-Michael addition of azoles to 4-(diphenylphosphoryl)but-3-en-2-one”, Mendeleev Commun., 2016, Volume 26, Issue 1,Pages <nobr>75

This article is cited in 6 papers

Communications

Regioselective aza-Michael addition of azoles to 4-(diphenylphosphoryl)but-3-en-2-one

M. A. Galkina^a, G. V. Bodrin^a, E. I. Goryunov^a, I. B. Goryunova^a, A. S. Sherstneva^a, J. S. Urmambetova^a, N. G. Kolotyrkina^b, M. M. Il'in^a, V. K. Brel^a, K. A. Kochetkov^a

^a A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
^b N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

Abstract: Aza-Michael reaction of (E)-4-(diphenylphosphoryl)but-3-en-2-one with mono- and bicyclic nitrogen heterocycles proceeds regioselectively in the absence of catalysts to give the corresponding ß-diphenylphosphoryl-b-azahetarylalkanones. Its reaction with imidazole in the presence of chiral organocatalysts affords the corresponding enantiomerically enriched adduct in higher yield.

Language: English

DOI: 10.1016/j.mencom.2016.01.029