Iterative multifunctionalization of unactivated C-H bonds in piperidines by way of intramolecular Rh(II)-catalyzed aminations |
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Authors: | Toumieux Sylvestre Compain Philippe Martin Olivier R |
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Affiliation: | Institut de Chimie Organique et Analytique, CNRS UMR 6005, Université d'Orléans, BP 6759, 45067 Orléans, France. |
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Abstract: | Efficient stereocontrolled synthesis of di-, tri-, tetra-, and pentasubstituted piperidines from simple 2-sulfamoyloxymethyl piperidine derivatives has been performed by way of intramolecular Rh-catalyzed amination of saturated C-H bonds. In this process, the sulfamoyloxymethyl arm was directly or indirectly involved in the functionalization of every saturated methylene group of the piperidine ring at C-3, C-4, C-5, and C-6. Direct application to the total synthesis of iminosugars and related compounds demonstrated the synthetic potential of this strategy. |
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