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
收藏
页码：107 / 110
页数：4
相关论文
共 50 条
  • [1] USE OF SHIFT-REAGENT WITH MTPA DERIVATIVES IN H-1-NMR SPECTROSCOPY .8. DETERMINATION OF ABSOLUTE-CONFIGURATION AND ENANTIOMERIC PURITY OF SPIROCYCLIC ALCOHOLS BY H-1-NMR
    KABUTO, K
    YASUHARA, F
    YAMAGUCHI, S
    TETRAHEDRON LETTERS, 1984, 25 (50) : 5801 - 5804
  • [2] DETERMINATION OF ABSOLUTE-CONFIGURATION OF CHIRAL THIOLS BY H-1-NMR SPECTROSCOPY OF DIASTEREOMERIC THIOL ESTERS
    HELMCHEN, G
    SCHMIERER, R
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (11): : 703 - 704
  • [3] DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF U-FAC-[CO(IDA)(MDIEN)]+ BY H-1-NMR SPECTROSCOPY
    AMA, T
    KAIZAKI, S
    KAWAGUCHI, H
    YASUI, T
    CHEMISTRY LETTERS, 1987, (03) : 441 - 444
  • [4] ASSIGNMENT OF ABSOLUTE-CONFIGURATION OF 2-SUBSTITUTED-1-PROPANOLS BY H-1-NMR SPECTROSCOPY
    YASUHARA, F
    YAMAGUCHI, S
    KASAI, R
    TANAKA, O
    TETRAHEDRON LETTERS, 1986, 27 (34) : 4033 - 4034
  • [5] Utilization of 1H NMR in the determination of absolute configuration of alcohols
    Barreiros, Marizeth L.
    David, Jorge M.
    David, Juceni P.
    QUIMICA NOVA, 2005, 28 (06): : 1061 - 1065
  • [6] DETERMINATION OF ABSOLUTE-CONFIGURATION OF STEREOGENIC CARBINOL CENTERS IN ANNONACEOUS ACETOGENINS BY H-1-NMR AND F-19-NMR MOSHER ESTER ANALYSIS
    HUI, Y
    RUPPRECHT, JK
    RIESER, MJ
    KOZLOWSKI, JF
    WOOD, KV
    MCLAUGHLIN, JL
    HOYE, TR
    HANSON, PR
    ZHUANG, Z
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 548 - ORGN
  • [7] A H-1-NMR METHOD FOR THE DETERMINATION OF ENANTIOMERIC EXCESS AND ABSOLUTE-CONFIGURATION OF CIS-DIHYDRODIOL METABOLITES OF POLYCYCLIC ARENES AND HETEROARENES
    BOYD, DR
    SHARMA, ND
    BOYLE, R
    MCMORDIE, RAS
    CHIMA, J
    DALTON, H
    TETRAHEDRON LETTERS, 1992, 33 (09) : 1241 - 1244
  • [8] DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF COMPLEX K[CO((S)-PRO)2CO3] BY H-1-NMR SPECTROSCOPY
    HAJEK, B
    SRANK, Z
    SYKOROVA, D
    INORGANICA CHIMICA ACTA-LETTERS, 1983, 76 (01): : L50 - L50
  • [9] DETERMINATION OF ABSOLUTE-CONFIGURATION OF STEREOGENIC CARBINOL CENTERS IN ANNONACEOUS ACETOGENINS BY H-1-NMR AND F-19-NMR ANALYSIS OF MOSHER ESTER DERIVATIVES
    RIESER, MJ
    HUI, YH
    RUPPRECHT, JK
    KOZLOWSKI, JF
    WOOD, KV
    MCLAUGHLIN, JL
    HANSON, PR
    ZHUANG, ZP
    HOYE, TR
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) : 10203 - 10213
  • [10] CHEMOENZYMATIC SYNTHESIS OF CHIRAL BORONATES FOR THE H-1-NMR DETERMINATION OF THE ABSOLUTE-CONFIGURATION AND ENANTIOMERIC EXCESS OF BACTERIAL AND SYNTHETIC CIS-DIOLS
    RESNICK, SM
    TOROK, DS
    GIBSON, DT
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11): : 3546 - 3549
12345