Determining factors in the assignment of the absolute configuration of alcohols by NMR. The use of anisotropic effects on remote positions.

被引：58

作者：

Seco, JM ^{[1
]}

Latypov, SK

Quinoa, E

Riguera, R

机构：

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

[2] RUSSIAN ACAD SCI, INST ORGAN & PHYS CHEM, KAZAN 420083, TATARSTAN, RUSSIA

来源：

TETRAHEDRON | 1997年 / 53卷 / 25期

关键词：

D O I：

10.1016/S0040-4020(97)00512-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The factors governing the efficiency of arylmethoxyacetic acids (AMAAs) For the determination of the absolute configuration of alcohols by NMR, have been identified and their influence studied. The largest Delta delta(RS) values are obtained either increasing the size of the aryl ring (i.e. alpha-(9-anthryl)-alpha-methoxyacetic acid, 5), or the population of the most stable conformer (i.e. reagent 3 at low temperature). The use of 5 to induce useful shifts on remote protons of complex molecules (i.e. androsterone) is described.

引用

页码：8541 / 8564

页数：24

共 31 条

[1] RING CURRENTS, LOCAL ANISOTROPY, AND PROBLEM OF OUT-OF-PLANE PROTONS - REINVESTIGATION OF NUCLEAR MAGNETIC-RESONANCE SPECTRUM OF [10]-PARACYCLOPHANE [J].

AGARWAL, A ;

BARNES, JA ;

FLETCHER, JL ;

MCGLINCHEY, MJ ;

SAYER, BG .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (13) :2575-2581

[2] IMPORTANCE OF LOCAL ANISOTROPIC EFFECTS AND RING CURRENTS ON PROTON SHIELDINGS IN AROMATIC-HYDROCARBONS [J].

BARFIELD, M ;

GRANT, DM ;

IKENBERRY, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (24) :6956-6961

[3]

CIOSLOWSKI J, 1987, QCPE B, V7, P159

[4] CHEMICAL SHIFTS RING CURRENTS + MAGNETIC ANISOTROPY IN AROMATIC HYDROCARBONS [J].

DAILEY, BP .

JOURNAL OF CHEMICAL PHYSICS, 1964, 41 (08) :2304-+

[5] THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].

DEWAR, MJS ;

ZOEBISCH, EG ;

HEALY, EF ;

STEWART, JJP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909

[6]

Eliel E.L., 1994, Stereochemistry of Organic Compounds

[7]

Frisch MJ, 1992, GAUSSIAN 92

[8] NOE CORRELATIONS IN MTPA, MNCB AND MBNC ESTERS [J].

FUKUSHI, Y ;

YAJIMA, C ;

MIZUTANI, J .

TETRAHEDRON LETTERS, 1994, 35 (50) :9417-9420

[9] A new NMR chiral derivatizing reagent for determining the absolute configurations of carboxylic acids [J].

Fukushi, Y ;

Shigematsu, K ;

Mizutani, J ;

Tahara, S .

TETRAHEDRON LETTERS, 1996, 37 (27) :4737-4740

[10] A NEW METHOD FOR ESTABLISHMENT OF ABSOLUTE-CONFIGURATIONS OF SECONDARY ALCOHOLS BY NMR-SPECTROSCOPY [J].

FUKUSHI, Y ;

YAJIMA, C ;

MIZUTANI, J .

TETRAHEDRON LETTERS, 1994, 35 (04) :599-602

← 1 2 3 4 →