Abstract
The gold(I)-catalyzed Claisen-type rearrangement of cyclic 8-aryl-2,7-enyn-l-ols proceeds via a cationic allylic vinyl ether gold intermediate to give spirocyclic ketones. The reaction proceeded via attack of the hydroxyl group onto the gold-activated alkynes followed by [3,3]-sigmatropic rearrangement to generate the spirocyclic ketones. This transformation can be applied to the synthesis of aza- and oxaspirocyclic ketones from cyclic 8-aryl-2,7-enyn-l-ols bearing an N-sulfonamide or an oxygen atom linkage in the tether and the gold(I) catalyst.
| Original language | English |
|---|---|
| Pages (from-to) | 160-166 |
| Number of pages | 7 |
| Journal | Organometallics |
| Volume | 29 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 2010 Jan 11 |
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
Fingerprint Dive into the research topics of 'Facile synthesis of spirocyclic ketones via gold(I)-catalyzed claisen-type rearrangement of cyclic 8-aryl-2,7-enyn-l-ols'. Together they form a unique fingerprint.
Cite this
Yeh, M-C. P., Pai, H. F., Hsiow, C. Y., & Wang, Y. R. (2010). Facile synthesis of spirocyclic ketones via gold(I)-catalyzed claisen-type rearrangement of cyclic 8-aryl-2,7-enyn-l-ols. Organometallics, 29(1), 160-166. https://doi.org/10.1021/om900833k