Collect. Czech. Chem. Commun. 2008, 73, 1814-1824

Use of Cyclic α,β-Unsaturated Trifluoromethyl Sulfones in Diels-Alder Reactions and Michael Additions

Thierry Billarda,*, Bernard R. Langloisa, Michael Essersb and Günter Haufeb,*

a ICBMS, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, Equipe SERCOF, 43 boulevard du 11 novembre 1918, Villeurbanne, F-69622, France; CNRS, UMR5246, Villeurbanne, F-69622, France; Université de Lyon, Lyon, F-69622, France; Université Lyon 1, Lyon, F-69622, France; INSA-Lyon, Villeurbanne, F-69622, France; CPE Lyon, Villeurbanne, F-69616, France
b Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Correnstrasse 40, D-48149 Münster, Germany


Vinylic trifluoromethyl triflones, in particular cyclic ones, constitute potentially valuable building-blocks for further syntheses. Their uses in Diels-Alder cycloadditions as dienophiles or dienes led only to moderate yields of expected products. However, under fluoride activation, they afforded unexpected tricycle compounds.

Keywords: α,β-Unsaturated trifluoromethyl sulfones; Vinyl triflones; Michael additions; Diels-Alder cycloaddition; Trifluoromethanesulfinate; Bicyclic compounds; Spirocyclic compounds.

References: 30 live references.