Addition of lithium ethyl fluoroacetate to cis and trans α,β-epoxyaldehydes. Access to C2 fluorinated butyrolactones |
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Authors: | Magalie ColletMichel Baltas Alexandre MartinezCécile Dehoux-Baudoin Liliane Gorrichon |
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Institution: | LSPCMIB, UMR 5068, Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse, France |
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Abstract: | The aldolisation reaction of lithium ethyl fluoroacetate with cis and trans α,β-epoxyaldehydes in their racemic forms proceeds with good C3-OH diastereoselectivity and much less at the C2-F carbon atom. A two-step reaction on the major aldol compounds (iodination, lactonisation) led to racemic functionalised C2 fluorinated lactones, possessing a C2/C3cis relationship between the fluorine and hydroxyl groups. |
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Keywords: | epoxyaldehydes aldolisation 2-fluorobutyrolactones |
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