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

[21] H-1-NMR CONFIGURATIONAL CORRELATION FOR RETRO-INVERSO DIPEPTIDES - APPLICATION TO THE DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF ENKEPHALINASE INHIBITORS - RELATIONSHIPS BETWEEN STEREOCHEMISTRY AND ENZYME RECOGNITION
FOURNIEZALUSKI, MC
LUCASSOROCA, E
DEVIN, J
ROQUES, BP
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (05) : 751 - 757
[22] LOW-TEMPERATURE H-1-NMR SPECTRA OF ASSOCIATED NORMAL-BUTANOL IN SOLUTION
GOLUBEV, NS
BUREIKO, SF
DENISOV, GS
JOURNAL OF MOLECULAR LIQUIDS, 1984, 28 (03) : 159 - 164
[23] CD AND H-1-NMR STUDY OF THE ROTATIONAL POPULATION DEPENDENCE OF THE HYDROXYMETHYL GROUP IN BETA-GLUCOPYRANOSIDES ON THE AGLYCON AND ITS ABSOLUTE-CONFIGURATION
MORALES, EQ
PADRON, JI
TRUJILLO, M
VAZQUEZ, JT
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (08): : 2537 - 2548
[24] A NON-SYMMETRICAL DIESTER OF 1(R)-AMINO-1-PHENYLMETHANEPHOSPHONIC ACID .2. THE DETERMINATION OF ABSOLUTE-CONFIGURATION AT THE CHIRAL PHOSPHORUS CENTER BY H-1-NMR STUDIES
SZEWCZYK, J
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1983, 16 (03): : 365 - 369
[25] A very reliable method for determination of absolute configuration of chiral secondary alcohols by 1H NMR spectroscopy
Takeuchi, Y
Fujisawa, H
Noyori, R
ORGANIC LETTERS, 2004, 6 (24) : 4607 - 4610
[26] DETERMINATION OF THE ABSOLUTE-CONFIGURATION AND ENANTIOMERIC PURITY OF ALCOHOLS FROM THE C-13-NMR SPECTRA OF THE CORRESPONDING MTPA ESTERS
LEMIERE, GL
WILLAERT, JJ
DOMMISSE, RA
LEPOIVRE, JA
ALDERWEIRELDT, FC
CHIRALITY, 1990, 2 (03) : 175 - 184
[27] The assignment of the absolute configuration of 1,2-diols by low-temperature NMR of a single MPA derivative
Freire, F
Seco, JM
Quiñoá, E
Riguera, R
ORGANIC LETTERS, 2005, 7 (22) : 4855 - 4858
[28] LOW-TEMPERATURE H-1-NMR EVIDENCE OF THE FOLDING OF ISOLATED RIBONUCLEASE S-PEPTIDE
RICO, M
NIETO, JL
SANTORO, J
BERMEJO, FJ
HERRANZ, J
GALLEGO, E
FEBS LETTERS, 1983, 162 (02) : 314 - 319
[29] Determination of the absolute configuration and enantiomeric purity of chiral primary alcohols by H-1 NMR of 9-anthrylmethoxyacetates.
Ferreiro, MJ
Latypov, SK
Quinoa, E
Riguera, R
TETRAHEDRON-ASYMMETRY, 1996, 7 (08) : 2195 - 2198
[30] 1H NMR determination of absolute configuration of 1-or 2-aryl-substituted alcohols and amines by means of their diastereomers:: Novel separation technique of diastereomeric derivatives of pyridyl alcohols by extraction
Matsugi, M
Itoh, K
Nojima, M
Hagimoto, Y
Kita, Y
CHEMISTRY-A EUROPEAN JOURNAL, 2002, 8 (24) : 5551 - 5564

← 1 2 3 4 5 →