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Selective Syntheses of Δα,β and Δβ,γ Butenolides from Allylic Cyclopropenecarboxylates via Tandem Ring Expansion/[3,3]-Sigmatropic Rearrangements

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posted on 19.02.2016, 13:31 by Xiaocong Xie, Yi Li, Joseph M. Fox
Allylic cyclopropenecarboxylates undergo ring expansion reactions to give 2-allyloxyfuran intermediates, which subsequently rearrange to Δβ,γ butenolides via a Claisen rearrangement or to the corresponding Δα,β butenolides via further Cope rearrangement. Also described are methods for chirality transfer in the rearrangement of nonracemic allylic esters.

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