Synthesis of Fluorinated beta-Aminophosphonates and gamma-Lactams
- Egileak:
- Concepción Alonso, Marı́a González, Marı́a Fuertes, Gloria Rubiales, Jose Marı́a Ezpeleta, and Francisco Palacios
- Urtea:
- 2013
- Aldizkaria:
- The Journal of Organic Chemistry
- Liburukia:
- 78
- Hasierako orria - Amaierako orria:
- 3858 - 3866
- Deskribapena:
-
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.