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Inverse electron demand diels alder reactions of 4 6 di methyl 2 oxo 2h pyran 5 carboxylic acid esters and morpholino enamines regiospecific preparation of 3 substituted or 4 substituted 2 6 di methyl benzoates

Inverse electron demand diels alder reactions of 4 6 di methyl 2 oxo 2h pyran 5 carboxylic acid esters and morpholino enamines regiospecific preparation of 3 substituted or 4 substituted 2 6 di methyl benzoates

Journal of Organic Chemistry 48(25): 4869-4873

Previously, .alpha.-pyrones have been used as dienes in cycloaddition reactions with enamines to form adducts that, upon elimination of CO2 via a cycloreversion reaction and concomitant aromatization through amine elimination, provided substituted aryl derivatives; however, the regioselectivity of this reaction was not determined. The Diels-Alder reaction of methyl or ethyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate with morpholino enamines is regiospecific. By proper choice of enamine either of the isomeric 2,6-dimethylbenzoates may be obtained as a single product. In several cases a single regioisomeric dihydrobenzoate, which results from elimination of CO2 from the initial cycloadduct, was isolated and characterized [of possible ultility in pyrethroid synthesis].

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Accession: 005746184

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