Synthesis of highly substituted adamantanones from bicyclo[3.3.1]nonanes.
- Author(s): Jung, Michael E
- Lee, Gloria S
- et al.
Published Web Locationhttps://doi.org/10.1021/jo501368d
Trifluoromethanesulfonic acid and other electrophiles promote formation of the adamantanone core from the readily accessible 1,5-dimethyl-3,7-dimethylenebicyclo[3.3.1]nonan-9-one 2. Because adamantyl cation 3 can be trapped by a range of nucleophiles, including aromatic and heteroaromatic rings, alcohol, nitriles, and halides, access to a wide variety of functionality at the newly formed tertiary position is provided.