Stereoselective [2,3]-sigmatropic rearrangements of unstabilized nitrogen Ylides
by Gawley, Robert E.; Moon, Kwangyul
[GRAPHICS] The steric course of the [2,3]-rearrangement of several unstabilized nitrogen ylides has been investigated. The reactions proceed cleanly through an anti transition state, affording modest to good yields of a single diastereomer of the product. In two examples containing an N-cinnamyl group, a competing [1,2]-rearrangement affords a minor product.
- Journal
- Organic Letters
- Volume
- 9
- Issue
- 16
- Year
- 2007
- Start Page
- 3093
- ISBN/ISSN
- 1523-7052; 1523-7060
- PMID
- 17628071
- DOI
- 10.1021/ol071188v