Phosphonyl radical addition to enol ethers. The stereoselective synthesis of cyclic ethers

C M  Jessop; A F  Parsons; A  Routledge; D J  Irvine

doi:10.1016/j.tetlet.2004.04.173

Phosphonyl radical addition to enol ethers. The stereoselective synthesis of cyclic ethers

C M Jessop, A F Parsons, A Routledge, D J Irvine

Chemistry

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

Abstract

Addition of diethyl phosphite or diethyl thiophosphite to enol ethers, in the presence of a radical initiator, results in the regioselective synthesis of organophosphonate or phosphonothioate derivatives, respectively, under mild conditions. This method can be applied to the stereoselective formation of substituted tetrahydrofurans and tetrahydropyrans, on cyclisation of vinyl ethers bearing unsaturated side chains. (C) 2004 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	5095-5098
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2004.04.173
Publication status	Published - 21 Jun 2004

Keywords

cyclisation
phosphorus compounds
radicals and radical reactions
EFFICIENT SYNTHESIS
TETRONASIN M139603
VINYL
PHOSPHONOTHIOATES
TETRONOMYCIN
INHIBITORS
ALKENES
REAGENT
ANALOGS
OLEFINS

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10.1016/j.tetlet.2004.04.173

Cite this

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title = "Phosphonyl radical addition to enol ethers. The stereoselective synthesis of cyclic ethers",

abstract = "Addition of diethyl phosphite or diethyl thiophosphite to enol ethers, in the presence of a radical initiator, results in the regioselective synthesis of organophosphonate or phosphonothioate derivatives, respectively, under mild conditions. This method can be applied to the stereoselective formation of substituted tetrahydrofurans and tetrahydropyrans, on cyclisation of vinyl ethers bearing unsaturated side chains. (C) 2004 Elsevier Ltd. All rights reserved.",

keywords = "cyclisation, phosphorus compounds, radicals and radical reactions, EFFICIENT SYNTHESIS, TETRONASIN M139603, VINYL, PHOSPHONOTHIOATES, TETRONOMYCIN, INHIBITORS, ALKENES, REAGENT, ANALOGS, OLEFINS",

author = "Jessop, {C M} and Parsons, {A F} and A Routledge and Irvine, {D J}",

year = "2004",

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day = "21",

doi = "10.1016/j.tetlet.2004.04.173",

language = "English",

volume = "45",

pages = "5095--5098",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Phosphonyl radical addition to enol ethers. The stereoselective synthesis of cyclic ethers

AU - Jessop, C M

AU - Parsons, A F

AU - Routledge, A

AU - Irvine, D J

PY - 2004/6/21

Y1 - 2004/6/21

N2 - Addition of diethyl phosphite or diethyl thiophosphite to enol ethers, in the presence of a radical initiator, results in the regioselective synthesis of organophosphonate or phosphonothioate derivatives, respectively, under mild conditions. This method can be applied to the stereoselective formation of substituted tetrahydrofurans and tetrahydropyrans, on cyclisation of vinyl ethers bearing unsaturated side chains. (C) 2004 Elsevier Ltd. All rights reserved.

AB - Addition of diethyl phosphite or diethyl thiophosphite to enol ethers, in the presence of a radical initiator, results in the regioselective synthesis of organophosphonate or phosphonothioate derivatives, respectively, under mild conditions. This method can be applied to the stereoselective formation of substituted tetrahydrofurans and tetrahydropyrans, on cyclisation of vinyl ethers bearing unsaturated side chains. (C) 2004 Elsevier Ltd. All rights reserved.

KW - cyclisation

KW - phosphorus compounds

KW - radicals and radical reactions

KW - EFFICIENT SYNTHESIS

KW - TETRONASIN M139603

KW - VINYL

KW - PHOSPHONOTHIOATES

KW - TETRONOMYCIN

KW - INHIBITORS

KW - ALKENES

KW - REAGENT

KW - ANALOGS

KW - OLEFINS

U2 - 10.1016/j.tetlet.2004.04.173

DO - 10.1016/j.tetlet.2004.04.173

M3 - Article

SN - 0040-4039

VL - 45

SP - 5095

EP - 5098

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -