THE DIRECT SYNTHESIS OF 3 ENANTIOMERICALLY PURE DIASTEREOMERS OF 1-FERROCENYLALKYLAMINE FROM I-(-)-MENTHONE, AND THE UP-DOWN STEREOISOMERISM OF FERROCENE DERIVATIVES

被引：13

作者：

DEMHARTER, A ^{[1
]}

UGI, I ^{[1
]}

机构：

[1] TECH UNIV MUNICH,INST ORGAN CHEM,LICHTENBERGERSTR 4,W-8046 GARCHING,GERMANY

来源：

JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG | 1993年 / 335卷 / 03期

关键词：

D O I：

10.1002/prac.19933350306

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Three (6 a-c) of the four conceivable diastereomeric 1-ferrocenylalkylamines can be synthesized from I-(-)-menthone and ferrocene in high enantiomeric purity. The many potential applications of such compounds, including their use as chiral templates in diastereoselective four component condensations (4CC, Ugi Reaction) are examined. Furthermore, NMR evidence for the first example of up-down-isomerism, a new type of conformational stereoisomerism of ferrocene derivatives, is discussed.

引用

页码：244 / 254

页数：11

共 34 条

[11] RETENTIVE NUCLEOPHILIC SUBSTITUTION OF (R)-ALPHA-FERROCENYLETHYL ACETATE [J].

GOKEL, GW ;

UGI, IK .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (03) :191-&

[12] ASYMMETRIC HYDROGENATION OF TRISUBSTITUTED ACRYLIC ACIDS CATALYZED BY A CHIRAL (AMINOALKYL)FERROCENYLPHOSPHINE RHODIUM COMPLEX [J].

HAYASHI, T ;

KAWAMURA, N ;

ITO, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7876-7878

[13] ASYMMETRIC-SYNTHESIS CATALYZED BY TRANSITION-METAL COMPLEXES WITH FUNCTIONALIZED CHIRAL FERROCENYLPHOSPHINE LIGANDS [J].

HAYASHI, T ;

KUMADA, M .

ACCOUNTS OF CHEMICAL RESEARCH, 1982, 15 (12) :395-401

[14]

Hayashi T., 1985, ASYMMETRIC SYNTHESIS, V5, P147

[15] ONE-POT SYNTHESES OF ALPHA-FERROCENYLALKYLAMINES [J].

HERRMANN, R ;

UGI, I .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (12) :956-957

[16] THE ELECTROPHILIC SUBSTITUTION OF FERROCENE BY PROTONATED CARBONYL-COMPOUNDS [J].

HERRMANN, R ;

UGI, I .

TETRAHEDRON, 1981, 37 (05) :1001-1009

[17]

HERRMANN R, 1979, ANGEW CHEM, V91, P1023

[18]

HERRMANN R, UNPUB HOUBENWEYL, V22

[19] CARBOHYDRATES AS CHIRAL TEMPLATES - ASYMMETRIC UGI-SYNTHESIS OF ALPHA-AMINO-ACIDS USING GALACTOSYLAMINES AS THE CHIRAL MATRICES [J].

KUNZ, H ;

PFRENGLE, W .

TETRAHEDRON, 1988, 44 (17) :5487-5494

[20] STEREOSELECTIVE SYNTHESES .5. AND ISONITRILES .24. STEREOSELECTIVE FOUR-COMPONENT CONDENSATIONS OF ALPHA-FERROCENYLETHYLAMINE AND ITS ABSOLUTE CONFIGURATION [J].

MARQUARDING, D ;

HOFFMANN, P ;

HEITZER, H ;

UGI, I .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (07) :1969-+

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