A simple 13C NMR method for determination of the relative stereochemistry of 2,3-dialkylpentenoic acids and related compounds

被引：5

作者：

Hong, S ^{[1
]}

McIntosh, MC ^{[1
]}

机构：

[1] Univ Arkansas, Dept Chem & Biochem, Fayetteville, AR 72701 USA

来源：

TETRAHEDRON | 2001年 / 57卷 / 24期

基金：

美国国家卫生研究院;

关键词：

NMR; stereochemistry; configuration; conformation;

D O I：

10.1016/S0040-4020(01)00349-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The relative stereochemistry of 2,3-dialkylpentenoic acids and derivatives thereof can be easily determined by comparison of C-13 NMR spectra of the syn and anti isomers. The chemical shifts of several of the resonances of the anti isomer lie downfield relative to the syn isomer. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：5055 / 5060

页数：6

共 45 条

[1]

[Anonymous], ALDRICHIMICA ACTA

[2] ESTER-ENOLATE CLAISEN REARRANGEMENT OF ALPHA-AMINO-ACID DERIVATIVES [J].

BARTLETT, PA ;

BARSTOW, JF .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (20) :3933-3941

[3] STEREOCHEMICAL CONTROL OF THE YNAMINE-CLAISEN REARRANGEMENT [J].

BARTLETT, PA ;

HAHNE, WF .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (05) :882-883

[4] STEREOCHEMISTRY OF THE DEPROTONATION AND OF THE ALDOLIZATION REACTION OF DITHIOESTERS [J].

BESLIN, P ;

VALLEE, Y .

TETRAHEDRON, 1985, 41 (13) :2691-2705

[5] THE HETERO-COPE REARRANGEMENT IN ORGANIC-SYNTHESIS [J].

BLECHERT, S .

SYNTHESIS-STUTTGART, 1989, (02) :71-82

[6] CONSTITUENTS OF EUPOMATIA SPECIES .14. THE STRUCTURES OF EUPOMATILONE-1, EUPOMATILONE-2, EUPOMATILONE-3, EUPOMATILONE-4, EUPOMATILONE-5, EUPOMATILONE-6 AND EUPOMATILONE-7 ISOLATED FROM EUPOMATIA-BENNETTII [J].

CARROLL, AR ;

TAYLOR, WC .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (12) :1705-1714

[7] A NONRESOLUTIVE APPROACH TO THE PREPARATION OF CONFIGURATIONALLY PURE DIFUNCTIONAL MOLECULES [J].

CHILLOUS, SE ;

HART, DJ ;

HUTCHINSON, DK .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (27) :5418-5420

[8] HIGHLY ENANTIOSELECTIVE AND DIASTEREOSELECTIVE IRELAND-CLAISEN REARRANGEMENT OF ACHIRAL ALLYLIC ESTERS [J].

COREY, EJ ;

LEE, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (10) :4026-4028

[9] SYNTHESIS OF 24-METHYL-26-HYDROXYSTEROID SIDE-CHAINS - MODELS FOR STEREOCHEMICAL ASSIGNMENTS IN POLYHYDROXYLATED MARINE STEROIDS [J].

DAURIA, MV ;

DERICCARDIS, F ;

MINALE, L ;

RICCIO, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11) :2889-2893

[10] CARBANION-ACCELERATED CLAISEN REARRANGEMENTS .7. PHOSPHINE OXIDE AND PHOSPHONATE ANION STABILIZING GROUPS [J].

DENMARK, SE ;

MARLIN, JE .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :1003-1013

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