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

共 50 条

[41] A new approach for the determination of the absolute configuration of secondary alcohols by 1H NMR with O-substituted mandelate derivatives.
Chataigner, I
Lebreton, J
Durand, D
Guingant, A
Villiéras, J
TETRAHEDRON LETTERS, 1998, 39 (13) : 1759 - 1762
[42] DETERMINATION OF THE CONFIGURATION OF DIASTEREOMERIC ETHANE DERIVATIVES BY H-1-NMR AND C-13 NMR-SPECTROSCOPY
SOHAR, P
SCHNEIDER, G
ABRAHAM, G
HORVATH, T
MEHESFALVI, Z
ACTA CHIMICA ACADEMIAE SCIENTARIUM HUNGARICAE, 1980, 105 (03): : 201 - 207
[43] A novel determination method of the absolute configuration of 1-aryl-1-alkylalcohols and amines by an intramolecular CH/π shielding effect in 1H NMR
Matsugi, M
Itoh, K
Nojima, M
Hagimoto, Y
Kita, Y
TETRAHEDRON LETTERS, 2001, 42 (45) : 8019 - 8022
[44] LOW-TEMPERATURE H-1-NMR STUDY OF ELECTRONIC-STRUCTURE PARAMETERS (T(1)(E)T) IN ZIRCONIUM DIHYDRIDE
ZOGAL, OJ
VUORIMAKI, AH
YLINEN, EE
NIEDZWIEDZ, K
ZEITSCHRIFT FUR PHYSIK B-CONDENSED MATTER, 1995, 96 (03): : 293 - 295
[45] DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF CHIRAL SECONDARY ALCOHOLS FROM "TETRA-O-ACETYLGLUCOSIDATION-INDUCED H-1 NUCLEAR MAGNETIC-RESONANCE SHIFTS
FAGHIH, R
FONTAINE, C
HORIBE, I
IMAMURA, PM
LUKACS, G
OLESKER, A
SEO, S
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (24): : 4918 - 4920
[46] Synthesis and H-1 NMR analysis of alpha-methoxy-alpha-difluoromethylphenylacetic acid derivatives of secondary alcohols for determination of absolute stereochemistry.
Hoye, RC
Braun, PD
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 213 : 438 - CHED
[47] Absolute Configuration of Ketone Cyanohydrins by 1H NMR: The Special Case of Polar Substituted Tertiary Alcohols
Louzao, Iria
Garcia, Rosa
Manuel Seco, Jose
Quinoa, Emilio
Riguera, Ricardo
ORGANIC LETTERS, 2009, 11 (01) : 53 - 56
[48] Practical enantioresolution of alcohols with 2-methoxy-2-(1-naphthyl)propionic acid and determination of their absolute configurations by the 1H NMR anisotropy method
Taji, H
Kasai, Y
Sugio, A
Kuwahara, S
Watanabe, M
Harada, N
Ichikawa, A
CHIRALITY, 2002, 14 (01) : 81 - 84
[49] ON TERPENES .297. ARCTOLIDE-REVISION OF ITS STEREOSTRUCTURE AND DETERMINATION OF ABSOLUTE-CONFIGURATION - DETAILED H-1 AND C-13 NMR ANALYSIS
BUDESINSKY, M
SAMAN, D
PELNAR, J
VASICKOVA, S
DROZDZ, B
GRABARCZYK, H
PHUONG, LVN
HOLUB, M
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1989, 54 (01) : 166 - 188
[50] DETERMINATION OF DIASTEREOMERIC PURITY AND ABSOLUTE-CONFIGURATION AT PHOSPHORUS OF TBUTYL-PHENYL-PHOSPHINIC ACID (-)-MENTHYL ESTER BY MEANS OF H-1 NMR-SPECTROSCOPY
LUCKENBACH, R
BECHTOLSHEIMER, HH
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1977, 32 (05): : 589 - 593

← 1 2 3 4 5 →