Inverse electron demand Diels-Alder reactions of 4, 6-dimethyl-2-oxo-2H-pyran-5-carboxylic acid esters and morpholino enamines: regiospecific preparation of 3-or 4- …

…, DM Roush, WA Van Saun

Index: Gingrich, Henry L.; Roush, David M.; Saun, William A. Van Journal of Organic Chemistry, 1983 , vol. 48, # 25 p. 4869 - 4873

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Citation Number: 16

Abstract

Previously, a-pyrones have been used as dienes in cycloaddition reactions with enamines to form adducts that, upon elimination of carbon dioxide via a cycloreversion reaction and concomitant aromatization through amine elimination, provided substituted aryl derivatives; however, the regioselectivity of this reaction was not determined. We report that the Diels- Alder reaction of methyl or ethyl 4, 6-dimethyl-2-oxo-2H-pyran-5-carboxylate with ...