An asymmetric aminohydroxylation route to cis-2,6-disubstituted piperidine-3-ol: application to the synthesis of (-)-deoxocassine

Article abstract of DOI:10.1016/j.tet.2006.08.014

A highly efficient, flexible, and convergent route to cis-2,3,6-trisubstituted piperidines has been developed employing the Sharpless asymmetric aminohydroxylation and stereoselective reductive amination by catalytic hydrogenation as the key steps. Its usage is illustrated by the short synthesis of the piperidine-3-ol alkaloid, (-)-deoxocassine.