Samarium diiodide-mediated intramolecular cyclodimerisation of bis-alpha,beta-unsaturated carbonyl compounds

Jonathan R. Powell; Sally Dixon; Mark E. Light; Jeremy Dunbar Kilburn

doi:10.1016/j.tetlet.2009.03.031

Samarium diiodide-mediated intramolecular cyclodimerisation of bis-alpha,beta-unsaturated carbonyl compounds

Jonathan R. Powell, Sally Dixon, Mark E. Light, Jeremy Dunbar Kilburn

University of Southampton

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

9 Citations (Scopus)

Abstract

Samarium(II) diiodide-mediated intramolecular cycloclimerisation of simple bis-enones and -enoates in THF/MeOH has been investigated. Spirocyclic and elaborated polycyclic products, including stereodefined cis-bicyclo[3.3.0]octane and trans-bicyclo[4.3.0]nonanes, are obtained in synthetically useful yield. (C) 2009 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	3564-3567
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	26
Early online date	13 Mar 2009
DOIs	https://doi.org/10.1016/j.tetlet.2009.03.031
Publication status	Published - 1 Jul 2009

Bibliographical note

We thank the EPSRC for a studentship (J.R.P.).

Keywords

ALPHA,BETA-UNSATURATED KETONES
REDUCTIVE CYCLIZATION
ACID-DERIVATIVES
ENONES
HYDRODIMERIZATION
IODIDE
HMPA

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title = "Samarium diiodide-mediated intramolecular cyclodimerisation of bis-alpha,beta-unsaturated carbonyl compounds",

abstract = "Samarium(II) diiodide-mediated intramolecular cycloclimerisation of simple bis-enones and -enoates in THF/MeOH has been investigated. Spirocyclic and elaborated polycyclic products, including stereodefined cis-bicyclo[3.3.0]octane and trans-bicyclo[4.3.0]nonanes, are obtained in synthetically useful yield. (C) 2009 Elsevier Ltd. All rights reserved.",

keywords = "ALPHA,BETA-UNSATURATED KETONES, REDUCTIVE CYCLIZATION, ACID-DERIVATIVES, ENONES, HYDRODIMERIZATION, IODIDE, HMPA",

author = "Powell, {Jonathan R.} and Sally Dixon and Light, {Mark E.} and Kilburn, {Jeremy Dunbar}",

note = "We thank the EPSRC for a studentship (J.R.P.). ",

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doi = "10.1016/j.tetlet.2009.03.031",

language = "English",

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T1 - Samarium diiodide-mediated intramolecular cyclodimerisation of bis-alpha,beta-unsaturated carbonyl compounds

AU - Powell, Jonathan R.

AU - Dixon, Sally

AU - Light, Mark E.

AU - Kilburn, Jeremy Dunbar

N1 - We thank the EPSRC for a studentship (J.R.P.).

PY - 2009/7/1

Y1 - 2009/7/1

N2 - Samarium(II) diiodide-mediated intramolecular cycloclimerisation of simple bis-enones and -enoates in THF/MeOH has been investigated. Spirocyclic and elaborated polycyclic products, including stereodefined cis-bicyclo[3.3.0]octane and trans-bicyclo[4.3.0]nonanes, are obtained in synthetically useful yield. (C) 2009 Elsevier Ltd. All rights reserved.

AB - Samarium(II) diiodide-mediated intramolecular cycloclimerisation of simple bis-enones and -enoates in THF/MeOH has been investigated. Spirocyclic and elaborated polycyclic products, including stereodefined cis-bicyclo[3.3.0]octane and trans-bicyclo[4.3.0]nonanes, are obtained in synthetically useful yield. (C) 2009 Elsevier Ltd. All rights reserved.

KW - ALPHA,BETA-UNSATURATED KETONES

KW - REDUCTIVE CYCLIZATION

KW - ACID-DERIVATIVES

KW - ENONES

KW - HYDRODIMERIZATION

KW - IODIDE

KW - HMPA

U2 - 10.1016/j.tetlet.2009.03.031

DO - 10.1016/j.tetlet.2009.03.031

M3 - Article

SN - 0040-4039

VL - 50

SP - 3564

EP - 3567

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

Samarium diiodide-mediated intramolecular cyclodimerisation of bis-alpha,beta-unsaturated carbonyl compounds

Abstract

Bibliographical note

Keywords

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