DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF ORGANIC-COMPOUNDS BY MEANS OF NMR-SPECTROSCOPY - MODIFIED MOSHER METHOD

被引：57

作者：

KUSUMI, T

机构：

[1] Research Center for New Natural Resources of Drugs, Faculty of Pharmaceutical Sciences, University of Tokushima

来源：

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN | 1993年 / 51卷 / 06期

关键词：

ABSOLUTE CONFIGURATION; NMR; MTPA; MOSHER; CHIRALITY; ASYMMETRIC SYNTHESIS; AMINO ACID; ANISOTROPY;

D O I：

10.5059/yukigoseikyokaishi.51.462

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method to determine the absolute configuration of organic compounds is described. It is a modern variation of Mosher's method and is designated 'modified Mosher's method'. The method uses MTPA moiety as a chiral auxiliary, the phenyl group of which affects the chemical shifts of the protons in the molecule. The compound possessing a secondary alcohol moiety is esterified with (R) and (S)-MTPA acids, and the respective diastereomers are subjected to NMR analyses to assign the signals of as many protons as possible. The pattern of arrangement of DELTAdelta values defined as DELTAdelta=delta(S)-delta(R) for each proton leads to the absolute configuration of the compound in question. Versatility and limitation of this new method are discussed,

引用

页码：462 / 470

页数：9

共 17 条

[1] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS
DALE, JA
MOSHER, HS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) : 512 - 519
[2] FIUD JC, 1977, STEREOCHEMISTRY, V3
[3] Harada N., 1983, CIRCULAR DICHROIC SP
[4] STRUCTURE AND ABSOLUTE-CONFIGURATION OF ISOCLAVUKERIN-A, A COMPONENT FROM AN OKINAWAN SOFT CORAL
KUSUMI, T
HAMADA, T
HARA, M
ISHITSUKA, MO
GINDA, H
KAKISAWA, H
[J]. TETRAHEDRON LETTERS, 1992, 33 (15) : 2019 - 2022
[5] ELUCIDATION OF THE ABSOLUTE-CONFIGURATIONS OF AMINO-ACIDS AND AMINES BY THE MODIFIED MOSHER METHOD
KUSUMI, T
FUKUSHIMA, T
OHTANI, I
KAKISAWA, H
[J]. TETRAHEDRON LETTERS, 1991, 32 (25) : 2939 - 2942
[6] ABSOLUTE-CONFIGURATIONS OF CYTO-TOXIC MARINE CEMBRANOLIDES - CONSIDERATION OF MOSHERS METHOD
KUSUMI, T
OHTANI, I
INOUYE, Y
KAKISAWA, H
[J]. TETRAHEDRON LETTERS, 1988, 29 (37) : 4731 - 4734
[7] ELUCIDATION OF THE RELATIVE AND ABSOLUTE STEREOCHEMISTRY OF LOBATRIENE, A MARINE DITERPENE, BY A MODIFIED MOSHER METHOD
KUSUMI, T
HAMADA, T
ISHITSUKA, MO
OHTANI, I
KAKISAWA, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) : 1033 - 1035
[8] FORMAL TOTAL SYNTHESIS OF (-)-DENDROBINE USING ZIRCONIUM PROMOTED CYCLIZATION - DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF THE INTERMEDIARY TRICYCLIC KETONE
MORI, M
SAITOH, F
UESAKA, N
SHIBASAKI, M
[J]. CHEMISTRY LETTERS, 1993, (02) : 213 - 216
[9] TOTAL SYNTHESIS OF (-)-SANADAOL AND (+)-SANADAOL - THE ABSOLUTE-CONFIGURATION OF SANADAOL AND DICTYODIAL
NAGAOKA, H
KOBAYASHI, K
YAMADA, Y
[J]. TETRAHEDRON LETTERS, 1988, 29 (46) : 5945 - 5946
[10] HIGH-FIELD FT NMR APPLICATION OF MOSHER METHOD - THE ABSOLUTE-CONFIGURATIONS OF MARINE TERPENOIDS
OHTANI, I
KUSUMI, T
KASHMAN, Y
KAKISAWA, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) : 4092 - 4096

← 1 2 →