Synthesis of Fluorinated β‑Aminophosphonates and γ‑Lactams
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https://figshare.com/articles/dataset/Synthesis_of_Fluorinated_Aminophosphonates_and_Lactams/2422444
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The
functionalized polyfluorophosphorylated 1-azadienes I have been prepared by a Wittig reaction of ethyl glyoxalate and
perfluorophosphorylated conjugated phosphoranes, obtained by reaction
of phosphazenes and fluorinated acetylenic phosphonates. Subsequent
reduction of both carbon–carbon and carbon–nitrogen
double bonds of these 1-azadienes I affords the fluorine-containing
β-aminophosphonates II, with the syn β-aminophosphonate being obtained as the major diastereoisomer.
Base-mediated cyclocondensation of a diastereomeric mixture of aminophosphonates II leads exclusively to a new type of functionalized trans-γ-lactams III in a diastereoselective
way. A computational study has also been used to explain the observed
diastereoselectivity of these reactions.
创建时间:
2016-02-19



