Different enantioselective interaction pathways induced by derivatized quinines

被引：25

作者：

Uccello-Barretta, G ^{[1
]}

Balzano, F ^{[1
]}

Quintavalli, C ^{[1
]}

Salvadori, P ^{[1
]}

机构：

[1] CNR, Ctr Studio Macromol Stereordinate & Otticamente A, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 12期

关键词：

D O I：

10.1021/jo991661l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereochemistries in solution of the diastereoisomeric complexes formed by quinines modified at the hydroxyl site (9-O-acetylquinine; 9-O-(3,5-dimethoxyphenylcarbamate)quinine) or quinuclidine nitrogen (N-benzylquininium chloride) and each enantiomer of 2-(3',5'-dinitrobenzamido)-1-phenylethanol have been compared to those of the free compounds by H-1 NMR investigations. Completely different interaction models, also involving changes of the free state conformations, have been obtained.

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页码：3596 / 3602

页数：7

相关论文

共 61 条

[1]

[Anonymous], 1989, NUCL OVERHAUSER EFFE, DOI DOI 10.1002/MRC.1260280819

[2] DIHYDROQUINIDINE CONFORMATION REVISITED - VARIABLE-TEMPERATURE NMR AND CD SPECTROSCOPY, AND MOLECULAR MECHANICS COMPUTATIONS [J].

BERG, U ;

AUNE, M ;

MATSSON, O .

TETRAHEDRON LETTERS, 1995, 36 (12) :2137-2140

[3] CHIRAL STATIONARY PHASES AND CIRCULAR-DICHROISM DETECTION IN HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY - DETERMINATION OF STEREOCHEMICAL PURITY OF DRUGS [J].

BERTUCCI, C ;

ROSINI, C ;

PINI, D ;

SALVADORI, P .

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 1987, 5 (02) :171-176

[4] Conformational behavior of cinchonidine in different solvents:: A combined NMR and ab initio investigation [J].

Bürgi, T ;

Baiker, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (49) :12920-12926

[5] Highly efficient synthesis of fibrinogen receptor antagonist L-734,217 via a novel chemoselective silyl-mediated conjugate addition of delta-lactams to 4-vinylpyridine [J].

Chung, JYL ;

Hughes, DL ;

Zhao, DL ;

Song, ZG ;

Mathre, DJ ;

Ho, GJ ;

McNamara, JM ;

Douglas, AW ;

Reamer, RA ;

Tsay, FR ;

Varsolona, R ;

McCauley, J ;

Grabowski, EJJ ;

Reider, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01) :215-222

[6] A critical analysis of the mechanistic basis of enantioselectivity in the bis-cinchona alkaloid catalyzed dihydroxylation of olefins [J].

Corey, EJ ;

Noe, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (45) :11038-11053

[7] CONFORMATIONAL STUDY OF CINCHONA ALKALOIDS - A COMBINED NMR, MOLECULAR MECHANICS, AND X-RAY APPROACH [J].

DIJKSTRA, GDH ;

KELLOGG, RM ;

WYNBERG, H ;

SVENDSEN, JS ;

MARKO, I ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (21) :8069-8076

[8] CONFORMATIONAL STUDY OF CINCHONA ALKALOIDS - A COMBINED NMR AND MOLECULAR-ORBITAL APPROACH [J].

DIJKSTRA, GDH ;

KELLOGG, RM ;

WYNBERG, H .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) :6121-6131

[9]

DIJKSTRA GDH, 1989, RECL TRAV CHIM PAY B, V108, P195

[10] ANALYSIS OF WARFARIN ENANTIOMERS - CHROMATOGRAPHIC-SEPARATION OF 6 STEREOISOMERIC ESTERS PREPARED FROM (-)-(1S,2R,4R)-ENDO-1,4,5,6,7,7-HEXACHLOROBICYCLO[2,2,1]HEPT-5-ENE-2-CARBOXYLIC ACID [J].

DUKE, CC ;

CARTER, SR ;

HAMBLEY, TW ;

HOLDER, GM ;

CUTLER, DJ .

CHIRALITY, 1994, 6 (08) :670-680

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