V. F. Mironov, T. A. Baronova, M. N. Dimukhametov, R. R. Fayzullin, I. A. Litvinov, “The reaction of 4-(1,3,2-benzodioxaphosphol-2-yloxy)-3-tert-butylpent-4-en-2-one with hexafluoroacetone”, Mendeleev Commun., 2019, том 29, выпуск 5,страницы 506

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The reaction of 4-(1,3,2-benzodioxaphosphol-2-yloxy)-3-tert-butylpent-4-en-2-one with hexafluoroacetone

V. F. Mironov^ab, T. A. Baronova^ab, M. N. Dimukhametov^a, R. R. Fayzullin^a, I. A. Litvinov^a

^a A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of the Russian Academy of Sciences, Kazan, Russian Federation
^b A.M. Butlerov Chemistry Institute, Kazan Federal University, Kazan, Russian Federation

Аннотация: Catalytic (ZnCl2, Et3N) phosphorylation of tert-butylacetylacetone with 2-chloro-1,3,2-benzodioxaphosphole unexpectedly occurs with elimination of proton from the methyl group and leads to vinyloxyphosphole derivative, viz., 4-(1,3,2-benzodioxaphosphol-2-yloxy)-3-tert-butylpent-4-en-2-one. Its reaction with hexafluoroacetone gives a cage phosphorane as a result of subsequent chemoselective [4 + 2]- and [3 + 2]-cycloadditions with stereoselectivity above 95%.

Ключевые слова: chlorobenzodioxaphosphole, vinylphosphite, tert-butylacetylacetone, chlorotrimethylsilane, hexafluoroacetone, zinc chloride, cage phosphorane.

Язык публикации: английский

DOI: 10.1016/j.mencom.2019.09.009