Switching between Novel Samarium(II)-Mediated Cyclizations by a Simple Change in Alcohol Cosolvent

Thomas K. Hutton; Kenneth W. Muir; David J. Procter

doi:10.1021/ol0358399

Switching between Novel Samarium(II)-Mediated Cyclizations by a Simple Change in Alcohol Cosolvent

Thomas K. Hutton, Kenneth W. Muir, David J. Procter

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

Abstract

(Equation Presented) γ,δ-Unsaturated ketones undergo two very different stereoselective cyclization reactions mediated by samarium(II) iodide depending upon the alcohol cosolvent used in the reaction. Switching between an unprecedented aldol spirocyclization and a novel cyclobutanol-forming process can be achieved simply by changing the alcohol cosolvent from methanol to tert-butyl alcohol.

Original language	English
Pages (from-to)	4811-4814
Number of pages	3
Journal	Organic Letters
Volume	5
Issue number	25
DOIs	https://doi.org/10.1021/ol0358399
Publication status	Published - 11 Dec 2003

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10.1021/ol0358399

CCDC 208376: Experimental Crystal Structure Determination
Hutton, T. K. (Contributor), Muir, K. W. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2004
DOI: 10.5517/cc6ztts, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc6ztts&sid=DataCite
Dataset
CCDC 208375: Experimental Crystal Structure Determination
Hutton, T. K. (Contributor), Muir, K. W. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2004
DOI: 10.5517/cc6ztsr, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc6ztsr&sid=DataCite
Dataset
CCDC 228808: Experimental Crystal Structure Determination
Hutton, T. K. (Contributor), Muir, K. W. (Contributor) & Procter, D. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2004
DOI: 10.5517/cc7p2xw, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc7p2xw&sid=DataCite
Dataset

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@article{79d6688781b94368954edb36a5020e73,

title = "Switching between Novel Samarium(II)-Mediated Cyclizations by a Simple Change in Alcohol Cosolvent",

abstract = "(Equation Presented) γ,δ-Unsaturated ketones undergo two very different stereoselective cyclization reactions mediated by samarium(II) iodide depending upon the alcohol cosolvent used in the reaction. Switching between an unprecedented aldol spirocyclization and a novel cyclobutanol-forming process can be achieved simply by changing the alcohol cosolvent from methanol to tert-butyl alcohol.",

author = "Hutton, {Thomas K.} and Muir, {Kenneth W.} and Procter, {David J.}",

year = "2003",

month = dec,

day = "11",

doi = "10.1021/ol0358399",

language = "English",

volume = "5",

pages = "4811--4814",

journal = "Organic Letters",

issn = "1523-7052",

publisher = "American Chemical Society",

number = "25",

}

TY - JOUR

T1 - Switching between Novel Samarium(II)-Mediated Cyclizations by a Simple Change in Alcohol Cosolvent

AU - Hutton, Thomas K.

AU - Muir, Kenneth W.

AU - Procter, David J.

PY - 2003/12/11

Y1 - 2003/12/11

N2 - (Equation Presented) γ,δ-Unsaturated ketones undergo two very different stereoselective cyclization reactions mediated by samarium(II) iodide depending upon the alcohol cosolvent used in the reaction. Switching between an unprecedented aldol spirocyclization and a novel cyclobutanol-forming process can be achieved simply by changing the alcohol cosolvent from methanol to tert-butyl alcohol.

AB - (Equation Presented) γ,δ-Unsaturated ketones undergo two very different stereoselective cyclization reactions mediated by samarium(II) iodide depending upon the alcohol cosolvent used in the reaction. Switching between an unprecedented aldol spirocyclization and a novel cyclobutanol-forming process can be achieved simply by changing the alcohol cosolvent from methanol to tert-butyl alcohol.

U2 - 10.1021/ol0358399

DO - 10.1021/ol0358399

M3 - Article

SN - 1523-7052

VL - 5

SP - 4811

EP - 4814

JO - Organic Letters

JF - Organic Letters

IS - 25

ER -

Switching between Novel Samarium(II)-Mediated Cyclizations by a Simple Change in Alcohol Cosolvent

Abstract

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Datasets

CCDC 208376: Experimental Crystal Structure Determination

CCDC 208375: Experimental Crystal Structure Determination

CCDC 228808: Experimental Crystal Structure Determination

Cite this