erythro-1-Naphthyl-1-(2-piperidyl)methanol: synthesis, resolution, NMR relative configuration, and VCD absolute configuration.
erythro-1-Naphthyl-1-(2-piperidyl)methanol: synthesis, resolution, NMR relative configuration, and VCD absolute configuration.
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DOI：
10.1021/jo0345502
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发表时间：
2003-09
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通讯作者：
A. Solladié-Cavallo*;C. Marsol;M. Yaakoub;K. Azyat;A. Klein;M. Roje;C. Șuteu;T. B. Freedman;X. Cao;L. Nafie
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作者：
A. Solladié-Cavallo*;C. Marsol;M. Yaakoub;K. Azyat;A. Klein;M. Roje;C. Șuteu;T. B. Freedman;X. Cao;L. Nafie
1-萘基-1-(2-哌啶基)甲醇4的赤式异构体是一种有效的不对称多相氢化手性改性剂，通过两步获得主要异构体(95%)，而苏式异构体则可以通过三步获得主要异构体(67%)。 erythro-4 和 threo-4 在 CHIRALCEL OD-RH 柱上分离。 VCD显示，NMR确定为赤式的非对映体确实是赤式，并且CHIRALCEL OD-R或-RH柱上第一个洗脱的(-)-对映体具有(1R，2S)构型。 VCD 研究确定CDCl(3) 溶液中至少存在五种构象异构体。此外，VCD发现的这种(-)-(1R,2S)绝对构型与丙酮酸催化氢化成乳酸的预期立体结果一致，这支持了(+)-(1S,2R)分配。
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.