UNUSUAL BASE-INDUCED REARRANGEMENT OF EXO-9-OXABICYCLO[4.2.1]NON-7-ENE OXIDE TO EXO-8-HYDROXYBICYCLO[3.3.0]OCTAN-2-ONE

[摘要]：Reaction of exo-9-oxabicyclo[4.2.1]non-7-ene oxide with n-BuLi gives exo-8-hydroxybicyclo[3.3.0]octan-2-one. Potential reaction pathways for this unusual rearrangement were evaluated with the aid of computational studies. The process is proposed to proceed by elimination to a transient allene oxide, which rearranges to a trans-epoxide enolate before undergoing epoxide alpha-lithiation and transannular C-H insertion.

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