Synthesis of Fluorinated β-Aminophosphonates and γ-Lactams
2013
Alonso, Concepción | Gonzalez, Maria | Fuertes, Marı́a | Rubiales, Gloria | Ezpeleta, Jose Marı́a | Palacios, Francisco
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.
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