Pyranose-derived conjugated enals

Several pyranose derived dienes and pyranose derived conjugated enals were prepared and the stereochemical outcome of their cycloaddition reactions studied. The diene and the enal moiety were incorporated into the carbohydrate ring by different methods depending on the substitution pattern of the pyranose. The pyranosidic ring might act as a diene or dienophile in cycloaddition reactions, and as a 1-oxabutadiene system in hetero Diels-Alder reactions. The factors governing the stereoselectivities for each type of cycloaddition are rationalized. The role of die steieogenic allylic alkoxy substituents in the relative topicity of the reactions is analyzed. [Pg.33]

Lopez J. C., Lukacs G. Pyranose-Derived Dienes and Conjugated Enals. Preparation and Diels-Alder Cycloaddition Reactions ACS Symp. Ser. 1992 494 33-49 Keywords carbohydrate, befera-Diels-Alder reactions, stereoselectivity... [Pg.321]

J. C. Lopez and G. Lukacs, Pyranose-derived dienes and conjugated enals—preparation and Diels-Alder cycloaddition reactions, in Cycloaddition Reactions in Carbohydrate Chemistry, 1992, pp. 33-49. [Pg.262]

LOPEZ LUKACS Pyranose-Derived Dienes and Conjugated Enals... [Pg.41]

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