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J Am Chem Soc. 2010 Dec 8;132(48):17282-95. doi: 10.1021/ja107536w. Epub 2010 Nov 15.

Polarization of the pyridine ring: highly functionalized piperidines from tungsten-pyridine complex.

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Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904, USA.


The N-acetylpyridinium complex of {TpW(NO)(PMe3)} undergoes regio- and stereoselective reactions with a broad range of common organic nucleophiles, providing a family of 1,2-dihydropyridine (DHP) complexes of the form TpW(NO)(PMe3)(3,4-η(2)-DHP). The present study explores the elaboration of these systems into novel piperidines. The addition of an acid to the DHP complexes generates highly asymmetric π-allyl complexes that in turn react with a second nucleophile at either C3 or C5. The subsequent oxidative decomplexation of these materials yields several piperidinamides with unconventional substitution patterns.


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