Аннотация:Camphor 1 is one of the chartered natural compounds that exerted a significant influence on the development of synthetic and theoretical organic chemistry. The ability of camphor to undergo easy carbocationic transformations is one of its unique features. However, synthetically useful methods of stereo- or regioselective modification of camphor based on skeletal rearrangements of this molecule are limited to С(9) and С(10) sulfonation, С(9) bromination, and transformations to 1-substituted camphenes under the action of phosphorus chlorides PCl3/PCl5, or trifluoromethanesulfonic acid anhydrides.
In this work we show that CF3SO3H/(CF3CO)2O mediated acylation of camphor with benzoic acids is accompanied by cascade of alkyl and hydride shifts and clears a path to new type of polyfunctional isoborneols 2. Further transformation of 2 will be discussed.