NMR method for determination of enantiomeric purity of sulfinimines

被引：20

作者：

Ardej-Jakubisiak, Monika ^{[1
]}

Kawecki, Robert ^{[1
,2
]}

机构：

[1] Univ Podlasie, Inst Chem, PL-08110 Siedlce, Poland

[2] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

来源：

TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 23期

关键词：

D O I：

10.1016/j.tetasy.2008.11.023

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A simple method for the determination of enantiomeric purity of N-sulfinyl aldimines has been developed. The use of optically active BINOL, as a chiral solvating agent for sulfinimines, allowed LIS to resolve resonance signals of an imine proton in H-1 NMR spectra. The best results have been obtained using benzene as a solvent. Signal separations of about 8 Hz were achieved on a 500 MHz spectrometer. C-13 decoupling during H-1 acquisition may improve the precision of the integration. The method is applicable for t-butyl and p-tolylsulfinyl derivatives. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：2645 / 2647

页数：3

共 15 条

[1]

Allenmark S. G., 1991, CHROMATOGRAPHIC ENAN

[2] A facile synthesis of N-sulfinylaldimines [J].

Ardej-Jakubisiak, Monika ;

Kawecki, Robert ;

Swietlinska, Aneta .

TETRAHEDRON-ASYMMETRY, 2007, 18 (21) :2507-2509

[3]

Drabowicz J., 1989, SULFUR LETT, V10, P37

[4] N-tert-Butanesulfinyl imines:: Versatile intermediates for the asymmetric synthesis of amines [J].

Ellman, JA ;

Owens, TD ;

Tang, TP .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (11) :984-995

[5] Emerging methods for the rapid determination of enantiomeric excess [J].

Finn, MG .

CHIRALITY, 2002, 14 (07) :534-540

[6] Chiral non-racemic sulfinimines: versatile reagents for asymmetric synthesis [J].

Morton, Daniel ;

Stockman, Robert A. .

TETRAHEDRON, 2006, 62 (38) :8869-8905

[7] NMR DETERMINATION OF ENANTIOMERIC PURITY [J].

PARKER, D .

CHEMICAL REVIEWS, 1991, 91 (07) :1441-1457

[8]

Rothchild R, 2000, ENANTIOMER, V5, P457

[9] Quantitative 1H NMR method for the routine spectroscopic determination of enantiomeric purity of active pharmaceutical ingredients fenfluramine, sertraline, and paroxetine [J].

Salsbury, JS ;

Isbester, PK .

MAGNETIC RESONANCE IN CHEMISTRY, 2005, 43 (11) :910-917

[10] MUTUAL OPTICAL RESOLUTION OF BIS-BETA-NAPHTHOL AND SULFOXIDES - ABSOLUTE-CONFIGURATION AND CRYSTAL-STRUCTURE OF A 1-1 MOLECULAR-COMPLEX [J].

TODA, F ;

TANAKA, K ;

MAK, TCW .

CHEMISTRY LETTERS, 1984, (12) :2085-2088

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