A stereoselective synthetic entry to β-substituted α-[(trans)-vinyl] phosphonamides

Ona Illa, Sergio Celis, Aimée El-Kazzi, Heinz Gornitzka, Antoine Baceiredo, Vicenç Branchadell, Rosa M. Ortuño

Research output: Contribution to journalArticleResearchpeer-review


α-(trans-Vinyl) phosphonamides with different substituents at the β-position were stereoselectively synthesized in high yields by treatment of β-substituted α-epoxy-α-trimethylsilyl phosphines with oxidizing agents. The corresponding phosphonamides were unstable in most cases and underwent reductive elimination affording desilylated vinyl derivatives. In turn, α-epoxy phosphines resulted from the [1+2] addition of [bis(diisopropylamino)phosphino](trimethylsilyl)carbene 2 to aliphatic, aromatic, and heteroaromatic aldehydes. In this way, a great variety of vinyl compounds have been efficiently prepared through one-pot procedure. © 2009 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)2451-2454
Issue number12
Publication statusPublished - 21 Mar 2009


  • Epoxy phosphonamides
  • Reductive elimination
  • Stable carbene
  • Vinyl phosphonamides


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