Chemistry–A European Journal

Unsaturated aldehydes as alkene equivalents in the Diels–Alder reaction

E Taarning, R Madsen

Index: Taarning, Esben; Madsen, Robert Chemistry - A European Journal, 2008 , vol. 14, # 18 p. 5638 - 5644

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Citation Number: 25

Abstract

Abstract A one-pot procedure is described for using α, β-unsaturated aldehydes as olefin equivalents in the Diels–Alder reaction. The method combines the normal electron demand cycloaddition with aldehyde dienophiles and the rhodium-catalyzed decarbonylation of aldehydes to afford cyclohexenes with no electron-withdrawing substituents. In this way, the aldehyde group serves as a traceless control element to direct the cycloaddition reaction. ...