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Journal Article
Research Support, Non-U.S. Gov't
Palladium-Catalyzed Double Allylation of Sugar-Imines by Employing Tamaru-Kimura's Protocol: Access to Unnatural Iminosugars.
Organic Letters 2017 April 8
Conversion of vinyl pyranosylamine and vinyl furanosylamines to 2,6- and 2,5-disubstituted pyrrolidine and piperidine iminosugars, respectively, in one pot was developed using Kimura and Tamaru's procedure, where a Pd salt in the presence of Et2 Zn was used for the domino reaction. In this procedure, double allylation, which involves nucleophilic allylation-heterocyclization, took place to give desired nitrogen heterocycles. This strategy was further elaborated to synthesize some unnatural deoxycalystegines, hydroxylated pyrrolidines, piperidines, and indolizidine analogues.
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