title: Selective syntheses of Δ(α,β) and Δ(β,γ) butenolides from allylic cyclopropenecarboxylates via tandem ring expansion/[3,3]-sigmatropic rearrangements.
abstract: Allylic cyclopropenecarboxylates undergo ring expansion reactions to give 2-allyloxyfuran intermediates, which subsequently rearrange to Δ(β,γ) butenolides via a Claisen rearrangement or to the corresponding Δ(α,β) butenolides via further Cope rearrangement. Also described are methods for chirality transfer in the rearrangement of nonracemic allylic esters.
authors.affiliation: Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
authors.forename: Xiaocong
authors.initials: X
authors.lastname: Xie
authors.forename: Yi
authors.initials: Y
authors.lastname: Li
authors.forename: Joseph M
authors.initials: JM
authors.lastname: Fox
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D004952:Esters; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D003521:Cyclopropanes; D004952:Esters; C004511:butenolide; C030797:cyclopropane; D012238:Rhodium; D015107:4-Butyrolactone