Arabinosylamine in Asymmetric Syntheses of Chiral Piperidine Alkaloids.

The stereodifferentiating potential of arabinosyl aldimines was utilized in stereoselective syntheses of 2-substituted dehydropiperidinones and their further transformation to 2,6-cis-substituted piperidinones. The absolute configuration was proven by X-ray analysis and by the synthesis of the enantiomerically pure alkaloid (+)-dihydropinidine. The presented method offers the possibility to synthesize piperidine derivatives enantiomeric to those obtained by the application of the corresponding galactosylamine auxiliary.