erythro-1Napthyl-1-(2-piperidyl)methanol: synthesis, resolution NMR relative configuration, and VCD absolute configuration

The erythro isomer of 1-Napthyl-1-(2-piperidyl)methanol, an efficient chiral modifier for asymmetric heterogeneous hydrogenation, was obtained as the major isomer (95%) in two steps while the threo isomer can be obtained as the major isomer (67%) in three steps. It is shown that the diastereomer determined as the erythro by NMR was indeed the erythro and that the first eluted (-)-enantiomer on CHIRALCEL OD-R or -RH columns has the (1R,2S) configuration.