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Nucleophilic addition of Grignard reagents and organolithium species to a 3-silyloxy-3,4,5,6-tetrahydropyridine N-oxide provides trans-2,3-disubstituted N-hydroxypiperidines exclusively. The application of this methodology to the preparation of a diversity of useful trans-2-substituted-3-hydroxypiperidines, a concise synthesis of (+)-swainsonine, and an enantiopure 1-substituted quinolizidine of utility in target-directed synthesis is reported.


Glenn Archibald, Chih-Pei Lin, Peter Boyd, David Barker, Vittorio Caprio. A divergent approach to 3-piperidinols: a concise syntheses of (+)-swainsonine and access to the 1-substituted quinolizidine skeleton. The Journal of organic chemistry. 2012 Sep 21;77(18):7968-80

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PMID: 22891976

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