Synthesis of highly substituted adamantanones from bicyclo[3.3.1]nonanes
Jung, ME; Lee, GS
| HERO ID | 5415969 |
|---|---|
| In Press | No |
| Year | 2014 |
| Title | Synthesis of highly substituted adamantanones from bicyclo[3.3.1]nonanes |
| Authors | Jung, ME; Lee, GS |
| Journal | Journal of Organic Chemistry |
| Volume | 79 |
| Issue | 21 |
| Page Numbers | 10547-10552 |
| Abstract | 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. |
| Doi | 10.1021/jo501368d |
| Pmid | 25275940 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |