Functionalized cyclobutenes via multicomponent thermal [2 + 2] cycloaddition reactions

Helen M. Sheldrake; Timothy W. Wallace; Craig P. Wilson

doi:10.1021/ol051675f

Functionalized cyclobutenes via multicomponent thermal [2 + 2] cycloaddition reactions

Helen M. Sheldrake, Timothy W. Wallace, Craig P. Wilson

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Abstract

(Chemical Equation Presented) Enamine [2 + 2] cycloadditions can be achieved in useful yields simply by stirring a mixture of an aldehyde, diethylamine, a dialkyl fumarate, and potassium carbonate in acetonitrile at 25°C, conditions that are compatible with the presence of a potential leaving group on the β-position of the intermediate enamine. Methylation and elimination of the product cyclobutanes completes a mild nonphotochemical route to functionalized cyclobutenes. © 2005 American Chemical Society.

Original language	English
Pages (from-to)	4233-4236
Number of pages	3
Journal	Organic Letters
Volume	7
Issue number	19
DOIs	https://doi.org/10.1021/ol051675f
Publication status	Published - 15 Sept 2005

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CCDC 276887: Experimental Crystal Structure Determination
Sheldrake, H. M. (Contributor), Wallace, T. (Contributor) & Wilson, C. P. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2006
DOI: 10.5517/cc993vj, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc993vj&sid=DataCite
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title = "Functionalized cyclobutenes via multicomponent thermal [2 + 2] cycloaddition reactions",

abstract = "(Chemical Equation Presented) Enamine [2 + 2] cycloadditions can be achieved in useful yields simply by stirring a mixture of an aldehyde, diethylamine, a dialkyl fumarate, and potassium carbonate in acetonitrile at 25°C, conditions that are compatible with the presence of a potential leaving group on the β-position of the intermediate enamine. Methylation and elimination of the product cyclobutanes completes a mild nonphotochemical route to functionalized cyclobutenes. {\textcopyright} 2005 American Chemical Society.",

author = "Sheldrake, {Helen M.} and Wallace, {Timothy W.} and Wilson, {Craig P.}",

year = "2005",

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day = "15",

doi = "10.1021/ol051675f",

language = "English",

volume = "7",

pages = "4233--4236",

journal = "Organic Letters",

issn = "1523-7052",

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T1 - Functionalized cyclobutenes via multicomponent thermal [2 + 2] cycloaddition reactions

AU - Sheldrake, Helen M.

AU - Wallace, Timothy W.

AU - Wilson, Craig P.

PY - 2005/9/15

Y1 - 2005/9/15

N2 - (Chemical Equation Presented) Enamine [2 + 2] cycloadditions can be achieved in useful yields simply by stirring a mixture of an aldehyde, diethylamine, a dialkyl fumarate, and potassium carbonate in acetonitrile at 25°C, conditions that are compatible with the presence of a potential leaving group on the β-position of the intermediate enamine. Methylation and elimination of the product cyclobutanes completes a mild nonphotochemical route to functionalized cyclobutenes. © 2005 American Chemical Society.

AB - (Chemical Equation Presented) Enamine [2 + 2] cycloadditions can be achieved in useful yields simply by stirring a mixture of an aldehyde, diethylamine, a dialkyl fumarate, and potassium carbonate in acetonitrile at 25°C, conditions that are compatible with the presence of a potential leaving group on the β-position of the intermediate enamine. Methylation and elimination of the product cyclobutanes completes a mild nonphotochemical route to functionalized cyclobutenes. © 2005 American Chemical Society.

U2 - 10.1021/ol051675f

DO - 10.1021/ol051675f

M3 - Article

SN - 1523-7052

VL - 7

SP - 4233

EP - 4236

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Functionalized cyclobutenes via multicomponent thermal [2 + 2] cycloaddition reactions

Abstract

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CCDC 276887: Experimental Crystal Structure Determination

Cite this