erythro-1-Naphthyl-1-(2-piperidyl)methanol: synthesis, resolution, NMR relative configuration, and VCD absolute configuration.
The erythro isomer of 1-naphthyl-1-(2-piperidyl)methanol 4, 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. erythro-4 and threo-4 were resolved on a CHIRALCEL OD-RH column. It has been shown by VCD 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. The VCD studies identify the presence of at least five conformers in CDCl(3) solution. Moreover, this (-)-(1R,2S) absolute configuration found by VCD is consistent with the expected stereo-outcome of catalytic hydrogenation of pyruvate into lactate, which supported the (+)-(1S,2R) assignment.
Solladié-Cavallo
A
A
Laboratoire de Stéréochimie Organométallique, ECPM/Université Louis Pasteur, 67087 Strasbourg, France. cavallo@chimie.u-strasbg.fr
Marsol
C
C
Yaakoub
M
M
Azyat
K
K
Klein
A
A
Roje
M
M
Suteu
C
C
Freedman
T B
TB
Cao
X
X
Nafie
L A
LA
D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002942:Circular Dichroism; D006865:Hydrogenation; D008968:Molecular Conformation; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000605:Amino Alcohols; D009281:Naphthalenes; D010880:Piperidines; C482350:erythro-1-naphthyl-1-(2-piperidyl)methanol