DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF ALCOHOLS BY LOW-TEMPERATURE H-1-NMR OF ARYL(METHOXY)ACETATES

被引：49

作者：

SECO, JM ^{[1
]}

LATYPOV, S ^{[1
]}

QUINOA, E ^{[1
]}

RIGUERA, R ^{[1
]}

机构：

[1] UNIV SANTIAGO DE COMPOSTELA, DEPT QUIM ORGAN, E-15706 SANTIAGO, SPAIN

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 01期

关键词：

D O I：

10.1016/0957-4166(94)00364-H

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Aromatic shielding effects in esters of (R)- and (S)-aryl(methoxy)acetic acids (AMAAs) differ by a factor Delta delta(RS) which, due to changes in rotamer populations, was seen to increase in H-1 NMR spectra of esters of AMAAs 6 - 10 as NMR probe temperature (T) was decreased. For example, Delta delta(RS) for esters of 6 increased by more than 100% between T = 298 and T = 220 - 175 K (depending on the alcohol). By comparing Delta delta(RS) values obtained from low temperature H-1 NMR spectra of their esters with (R)- and (S)-AMAAs 6 - 10, the absolute configuration of chiral alcohols can be reliably assigned.

引用

页码：107 / 110

页数：4

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