Intramolecular Hetero-Diels-Alder Reaction of 3-Benzylidene-1,2-dicarbonyl Compounds

Lutz -F. Tietze; Thomas Brumby; Martina Pretor

doi:10.1055/s-1987-28049

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Synthesis 1987; 1987(8): 700-703
DOI: 10.1055/s-1987-28049

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Intramolecular Hetero-Diels-Alder Reaction of 3-Benzylidene-1,2-dicarbonyl Compounds

Lutz -F. Tietze^* , Thomas Brumby, Martina Pretor

^*Institut für Organische Chemie der Universität Göttingen, Tammannstr. 2, D-3400 Göttingen, West Germany

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Publication Date:
12 September 2002 (online)

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The intramolecular hetero-Diels-Alder reaction of benzylidene 2-oxocarboxylic acid esters 7 is described, and the diastereoselectivity of the reaction determined. Condensation of the aldehyde 1 with 2-oxocarboxylic acids 5a, b followed by esterification gives 7a, b which cyclize in refluxing xylene to 8a, b and 9a, b in better than 95% yield.