Iterative Multifunctionalization of Unactivated C−H Bonds in Piperidines by Way of Intramolecular Rh(II)-Catalyzed Aminations
The Journal of Organic Chemistry2008Vol. 73(6), pp. 2155–2162
Citations Over TimeTop 17% of 2008 papers
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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