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