Samarium diiodide mediated intramolecular cyclisation of mixed enone-enoate systems: a simple preparation of spirocyclic ethers

Junxiu Meng; Mark E. Light; Sally Dixon; Jeremy Dunbar Kilburn

doi:10.1016/j.tetlet.2010.12.077

Samarium diiodide mediated intramolecular cyclisation of mixed enone-enoate systems: a simple preparation of spirocyclic ethers

Junxiu Meng, Mark E. Light, Sally Dixon, Jeremy Dunbar Kilburn

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

2 Citations (Scopus)

Abstract

Samarium(II) diiodide mediated intramolecular cyclisation of mixed enone-enoate substrates in THF/MeOH is described. Spirocyclic ethers are obtained, and the stereodefined preparation of 1-oxaspiro[4.4]nonan-7-one products is included. (C) 2010 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	928-931
Number of pages	4
Journal	Tetrahedron Letters
Volume	52
Issue number	8
DOIs	https://doi.org/10.1016/j.tetlet.2010.12.077
Publication status	Published - 23 Feb 2011

Keywords

Samarium(II) diiodide
Reductive cyclisation
Michael addition
Spirocycle
Chelation control
LOW-VALENT TITANIUM
ELECTRON-TRANSFER
REDUCTIVE CYCLODIMERIZATION
SCILLA-SCILLOIDES
KETONES
HYDRODIMERIZATION
METAL
OLIGOGLYCOSIDES
IODIDE
ALPHA

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10.1016/j.tetlet.2010.12.077

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@article{e63defa1b8584f5e9b9dbc04795d92c1,

title = "Samarium diiodide mediated intramolecular cyclisation of mixed enone-enoate systems: a simple preparation of spirocyclic ethers",

abstract = "Samarium(II) diiodide mediated intramolecular cyclisation of mixed enone-enoate substrates in THF/MeOH is described. Spirocyclic ethers are obtained, and the stereodefined preparation of 1-oxaspiro[4.4]nonan-7-one products is included. (C) 2010 Elsevier Ltd. All rights reserved.",

keywords = "Samarium(II) diiodide, Reductive cyclisation, Michael addition, Spirocycle, Chelation control, LOW-VALENT TITANIUM, ELECTRON-TRANSFER, REDUCTIVE CYCLODIMERIZATION, SCILLA-SCILLOIDES, KETONES, HYDRODIMERIZATION, METAL, OLIGOGLYCOSIDES, IODIDE, ALPHA",

author = "Junxiu Meng and Light, {Mark E.} and Sally Dixon and Kilburn, {Jeremy Dunbar}",

year = "2011",

month = feb,

day = "23",

doi = "10.1016/j.tetlet.2010.12.077",

language = "English",

volume = "52",

pages = "928--931",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "PERGAMON-ELSEVIER SCIENCE LTD",

number = "8",

}

TY - JOUR

T1 - Samarium diiodide mediated intramolecular cyclisation of mixed enone-enoate systems

T2 - a simple preparation of spirocyclic ethers

AU - Meng, Junxiu

AU - Light, Mark E.

AU - Dixon, Sally

AU - Kilburn, Jeremy Dunbar

PY - 2011/2/23

Y1 - 2011/2/23

N2 - Samarium(II) diiodide mediated intramolecular cyclisation of mixed enone-enoate substrates in THF/MeOH is described. Spirocyclic ethers are obtained, and the stereodefined preparation of 1-oxaspiro[4.4]nonan-7-one products is included. (C) 2010 Elsevier Ltd. All rights reserved.

AB - Samarium(II) diiodide mediated intramolecular cyclisation of mixed enone-enoate substrates in THF/MeOH is described. Spirocyclic ethers are obtained, and the stereodefined preparation of 1-oxaspiro[4.4]nonan-7-one products is included. (C) 2010 Elsevier Ltd. All rights reserved.

KW - Samarium(II) diiodide

KW - Reductive cyclisation

KW - Michael addition

KW - Spirocycle

KW - Chelation control

KW - LOW-VALENT TITANIUM

KW - ELECTRON-TRANSFER

KW - REDUCTIVE CYCLODIMERIZATION

KW - SCILLA-SCILLOIDES

KW - KETONES

KW - HYDRODIMERIZATION

KW - METAL

KW - OLIGOGLYCOSIDES

KW - IODIDE

KW - ALPHA

U2 - 10.1016/j.tetlet.2010.12.077

DO - 10.1016/j.tetlet.2010.12.077

M3 - Article

VL - 52

SP - 928

EP - 931

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 8

ER -

Samarium diiodide mediated intramolecular cyclisation of mixed enone-enoate systems: a simple preparation of spirocyclic ethers

Abstract

Keywords

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