Lewis Acis Induced Ene Cyclization of ω-Olefinic Trifluoromethyl Ketones: Access to BIcyclic Compounds Bearing a CF3 Group

Article abstract of DOI:10.1021/jo00020a021

Lewis acid induced ene cyclization of ω-olefinic trifluoromethyl ketones provides (trifluoromethyl)decalins and (trifluoromethyl)hydrindans in high yield. δ-(1-Cyclohexenyl) trifluoromethyl ketone 1a leads stereoselectively to 1-(trifluoromethyl)-1-hydroxy-Δ^5,10-octalin 3a or 10-chloro-1-(trifluoromethyl)-1-hydroxydecalin 6a, depending on the choice of Lewis acid. γ-(1-Cyclohexenyl) trifluoromethyl ketone 2a leads to a mixture of 9-chloro-1-(trifluoromethyl)-1-hydroxyhydrindans 10a and 11a.Similar reactions were performed successfully with the corresponding β-keto esters 1b and 2b.