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Michael, Michael-annulation, and oxa-Diels-Alder reactions of carbohydrate derivatives that afford polyoxy-functionalized piperidine derivatives bearing tetrasubstituted carbon at the 3-position of the piperidine ring are reported. Iminium ions generated from carbohydrate… Click to show full abstract
Michael, Michael-annulation, and oxa-Diels-Alder reactions of carbohydrate derivatives that afford polyoxy-functionalized piperidine derivatives bearing tetrasubstituted carbon at the 3-position of the piperidine ring are reported. Iminium ions generated from carbohydrate derivatives with amines were converted to enamines in situ, which acted as nucleophiles. As a result, substituents were introduced at the 3-position or both 2- and 3-positions of the piperidines bearing polyoxy groups. This strategy will be useful in drug discovery efforts.
Journal Title: Organic letters
Year Published: 2020
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