1428368-22-2Relevant academic research and scientific papers
Synthesis of fluorinated β-aminophosphonates and γ-lactams
Alonso, Concepcion,Gonzalez, Maria,Fuertes, Maria,Rubiales, Gloria,Ezpeleta, Jose Maria,Palacios, Francisco
, p. 3858 - 3866 (2013/06/05)
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.
