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4-Toluenesulfonic acid: an environmentally benign catalyst for Nazarov cyclizations

✍ Scribed by Mukkanti Amere; Jérôme Blanchet; Marie-Claire Lasne; Jacques Rouden

Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
134 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis

An efficient metal-free catalytic protocol for the electrocyclization of a-alkoxydienones to cyclopentenones (Nazarov reaction) in near to quantitative yields is described. The key parameters are the use of inexpensive 4-toluenesulfonic acid in 5 mol % at room temperature in acetonitrile or under solvent-free conditions. The versatility of the transformation is demonstrated with unpolarized dienones with good regioselectivities and excellent yields.

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