Unprecedented alkene stereocontrol in the Claisen rearrangement of cyclic bis-allylic esters
by McFarland, Chris; Hutchison, John; McIntosh, Matthias C.
[GRAPHICS] The Ireland and ester enolate Claisen rearrangements of tertiary substituted bis-allylic esters derived from cyclohexenones afford pentenoic acids that possess tri- and tetrasubstituted alkylidenes with unprecedented levels of stereoselectivity. In some cases the higher energy exocyclic alkene is the major product.
- Journal
- Organic Letters
- Volume
- 7
- Issue
- 17
- Year
- 2005
- Start Page
- 3641-3644
- URL
- https://dx.doi.org/10.1021/ol0511732
- ISBN/ISSN
- 1523-7052; 1523-7060
- DOI
- 10.1021/ol0511732