N-(β,β-Difluorovinyl)oxazolidin-2-ones: First Synthesis and Application in [3+2]- and [4+2]-Cycloaddition-Type Reactions

Abstract

N-(β,β-Difluorovinyl)oxazolidin-2-ones were conveniently prepared in good yields in two steps from the parent oxazolidin-2-ones. The [3+2]- and [4+2]-cycloaddition-type reactions with electron-deficient partners were investigated as first application of these new enamides. TMSOTf was efficient in promoting these two reactions, and the corresponding heterocyclic difluoro adducts were obtained in high yields.

N-(β,β-difluorovinyl)oxazolidin-2-ones - trimethylsilyl trifluoromethanesulfonate - 1,3-dipolar cycloaddition - Diels-Alder reaction - dipolarophile - nitrone - heterodiene

References and Notes

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Procedures and compounds are described in the Supplementary Information.

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