V. Yu. Korotaev, V. Ya. Sosnovskikh, M. A. Barabanov, A. Yu. Barkov, M. I. Kodess, “Stereoselective tandem [4 + 2]/[3 + 2] cycloaddition reactions of 3,3,3-trichloro(trifluoro)-1-nitropropenes and 2,3-dihydrofuran”, Mendeleev Commun., 2010, Volume 20, Issue 1,Pages <nobr>17

This article is cited in 20 papers

Stereoselective tandem [4 + 2]/[3 + 2] cycloaddition reactions of 3,3,3-trichloro(trifluoro)-1-nitropropenes and 2,3-dihydrofuran

V. Yu. Korotaev^a, V. Ya. Sosnovskikh^a, M. A. Barabanov^a, A. Yu. Barkov^a, M. I. Kodess^b

^a Department of Chemistry, Ural Federal University, Ekaterinburg, Russian Federation
^b I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Ekaterinburg, Russian Federation

Abstract: The first example of the domino hetero-Diels–Alder/1,3-dipolar cycloaddition, in which 3,3,3-trichloro(trifluoro)-1-nitropropenes act as both the heterodiene and the dipolarophile in the reaction with 2,3-dihydrofuran, is described. The trichloromethylated nitroolefin gave tricyclic nitroso acetal as a single regio- and stereoisomer, while the trifluoromethylated derivative afforded a 3:1 mixture of two regioisomeric cycloadducts.

Language: English

DOI: 10.1016/j.mencom.2010.01.007