Regioselective electrophilic oxidation of a 5-amino-endo-tricyclo[5.2.1.02,6]decenyl enaminone. Synthesis of a novel heterocyclic compound

An unexpected tandem regioselective oxidation and cyclization of 5-((S)-2′-hydroxymethylpyrrolidin-1′-yl)-endo-tricyclo[5.2.1.02,6]deca-4,8-dien-3-ones 7 is reported. The reaction proceeds smoothly to afford novel tetracyclic compounds 8 and 9 in good yield, The structure of 8 was established by single-crystal X-ray analysis. Surprisingly, the C8C9 norbornene double bond remains intact under these oxidative conditions.