Rearrangement Approaches to Cyclic Skeletons. XII. Acid-Catalyzed Isomerization of Bicyclooct-6-en-2-ones into Bicyclooct-3-en-2-ones without Razemization

Article abstract of DOI:10.1246/bcsj.70.1919

The treatment of a bicyclo<3.2.1>oct-6-en-2-one (3) with Amberlyst<*> (H-15) in boiling benzene gave a mixture of bicyclo<3.2.1>oct-3-en-2-one (5) and bicyclo<2.2.2>oct-5-en-2-one (6).The ratio of 5 to 6 was influenced by the substituent at the C-1 position of the ketone 3.Chiral ketones 3 were transformed into the chiral α,β-unsaturated ketones 5 without racemization.