title: Unprecedented alkene stereocontrol in the Claisen rearrangement of cyclic bis-allylic esters.
abstract: 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. [reaction: see text]
authors.affiliation: Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, AR 72701, USA.
authors.forename: Chris
authors.initials: C
authors.lastname: McFarland
authors.forename: John
authors.initials: J
authors.lastname: Hutchison
authors.forename: Matthias C
authors.initials: MC
authors.lastname: McIntosh
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D003500:Cyclization; D004952:Esters; D008956:Models, Chemical; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D004952:Esters