Stereoselective [2,3]-sigmatropic rearrangements of unstabilized nitrogen ylides.
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.
Gawley
Robert E
RE
Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, Arkansas 72701, USA. bgawley@uark.edu
Moon
Kwangyul
K
D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism
D006571:Heterocyclic Compounds; D009584:Nitrogen