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

doi:10.1016/j.tet.2009.01.074

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

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

Abstract

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 language	English
Pages (from-to)	2451-2454
Journal	Tetrahedron
Volume	65
Issue number	12
DOIs	https://doi.org/10.1016/j.tet.2009.01.074
Publication status	Published - 21 Mar 2009

Keywords

Epoxy phosphonamides
Reductive elimination
Stable carbene
Vinyl phosphonamides

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10.1016/j.tet.2009.01.074

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

abstract = "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. {\textcopyright} 2009 Elsevier Ltd. All rights reserved.",

keywords = "Epoxy phosphonamides, Reductive elimination, Stable carbene, Vinyl phosphonamides",

author = "Ona Illa and Sergio Celis and Aim{\'e}e El-Kazzi and Heinz Gornitzka and Antoine Baceiredo and Vicen{\c c} Branchadell and Ortu{\~n}o, {Rosa M.}",

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TY - JOUR

T1 - A stereoselective synthetic entry to β-substituted α-[(trans)-vinyl] phosphonamides

AU - Illa, Ona

AU - Celis, Sergio

AU - El-Kazzi, Aimée

AU - Gornitzka, Heinz

AU - Baceiredo, Antoine

AU - Branchadell, Vicenç

AU - Ortuño, Rosa M.

PY - 2009/3/21

Y1 - 2009/3/21

N2 - 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.

AB - 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.

KW - Epoxy phosphonamides

KW - Reductive elimination

KW - Stable carbene

KW - Vinyl phosphonamides

U2 - 10.1016/j.tet.2009.01.074

DO - 10.1016/j.tet.2009.01.074

M3 - Article

SN - 0040-4020

VL - 65

SP - 2451

EP - 2454

JO - Tetrahedron

JF - Tetrahedron

IS - 12

ER -

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

Abstract

Keywords

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