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