Determination of the absolute stereochemistry of alcohols and amines by NMR of the group directly linked to the chiral derivatizing reagent

被引：19

作者：

Latypov, SK

Galiullina, NF

Aganov, AV

Kataeva, VE

Riguera, R

机构：

[1] Inst Organ & Phys Chem, Kazan 420083, Tatarstan, Russia

[2] Kazan State Univ, Fac Phys, Kazan 420008, Tatarstan, Russia

[3] Univ Santiago de Compostela, Dept Quim Organ, E-15706 Santiago, Spain

来源：

TETRAHEDRON | 2001年 / 57卷 / 11期

关键词：

absolute stereochemistry; NMR; chiral derivatizing reagents; methoxyphenylacetic acid; methoxytrifluoromethylphenylacetic acid;

D O I：

10.1016/S0040-4020(01)00056-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

NMR experiments and calculations (PM3) indicate that the asymmetry of the substrate (alcohol or amine) leads to the redistribution of the conformer populations of their methoxyphenylacetic acid (MPA) or methoxytrifluoromethylphenylacetic acid (MTPA) derivatives rather than to the distortion of the conformer geometry as was postulated by Mosher. An absolute configuration of secondary alcohols and primary amines can be determined according to the chemical shifts of the CalphaH protons in NMR spectra of their MPA derivatives. The CalphaH proton of the diastereomer having a greater relative population of the sp form should resonate at a lower held. (C) 2001 Elsevier Science Ltd. All rights reserved.

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页码：2231 / 2236

页数：6

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