Abstract
A novel gold(I)-catalyzed cascade cycloisomerization of a variety of propargylic esters leading to unsymmetrically substituted naphthalenes has been developed. This domino process involves an unprecedented tandem sequence of 1,3- and 1,2-migrations of two substantially different migrating groups. It is believed that this transformation proceeds via formation of 1,3-diene intermediate or its equivalent, which, upon carbocyclization and aromatization steps, transforms into the naphthalene skeleton. In addition, it was also demonstrated that a variety of 1,3-dienes can be accessed stereoselectively via the 1,3-migration-proton transfer cascade.
Original language | English (US) |
---|---|
Pages (from-to) | 1859-1870 |
Number of pages | 12 |
Journal | Tetrahedron |
Volume | 65 |
Issue number | 9 |
DOIs | |
State | Published - Feb 28 2009 |
Externally published | Yes |
Keywords
- 1,3-Dienes
- Gold
- Naphthalenes
- Propargylic esters
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry