Asymmetric hetero Diels-Alder reaction using chiral cationic metallosalen complexes as catalysts

被引：83

作者：

Aikawa, K ^{[1
]}

Irie, R ^{[1
]}

Katsuki, T ^{[1
]}

机构：

[1] Kyushu Univ, Grad Sch, Fac Sci, Dept Chem,Higashi Ku, Fukuoka 8128581, Japan

来源：

TETRAHEDRON | 2001年 / 57卷 / 05期

关键词：

cationic metallosalen complex; asymmetric catalysis; hetero Diels-Alder reaction; Danishefsky's diene;

D O I：

10.1016/S0040-4020(00)01048-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral cationic (R,S)- or (R,R)-(salen)-manganese(III) and -chromium(III) complexes served as the catalysts for asymmetric hetero Diels-Alder reaction of Danishefsky's diene with aldehydes, achieving high enantioselectivity (up to 97% ee at 0 degreesC). The reactions of aldehydes bearing no precoordinating functional group were well effected by using (R,R)-complexes as catalysts, while those of aldehydes bearing a precoordinating functionality were better effected by using (R,S)-complexes. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：845 / 851

页数：7

共 40 条

[1] CRYSTAL AND MOLECULAR STRUCTURE OF BENZOYLACETONATO-[NN'-ETHYLENEBIS-(SALICYLIDENEIMINATO)]COBALT(III)-1.5 WATER [J].

BAILEY, NA ;

MCKENZIE, ED ;

HIGSON, BM .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1972, (04) :503-&

[2] CHIRAL INDUCTION IN THE CYCLOCONDENSATION OF ALDEHYDES WITH SILOXYDIENES [J].

BEDNARSKI, M ;

MARING, C ;

DANISHEFSKY, S .

TETRAHEDRON LETTERS, 1983, 24 (33) :3451-3454

[3] INTERACTIVITY OF CHIRAL CATALYSTS AND CHIRAL AUXILIARIES IN THE CYCLOADDITION OF ACTIVATED DIENES WITH ALDEHYDES - A SYNTHESIS OF L-GLUCOSE [J].

BEDNARSKI, M ;

DANISHEFSKY, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) :7060-7067

[4] LIGAND PROPERTIES OF QUADRIDENTATE SCHIFFS BASES - CRYSTAL AND MOLECULAR STRUCTURE OF MIXED-LIGAND COMPLEX [NN'-ETHYLENEBIS-(SALICYLIDENEIMINATO)](ACETYLACETONATO)COBALT(III)-0.7 WATER [J].

CALLIGARIS, M ;

MANZINI, G ;

RANDACCIO, L ;

NARDIN, G .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1972, (04) :543-+

[5] ENANTIOSELECTIVE MUKAIYAMA-ALDOL AND ALDOL-DIHYDROPYRONE ANNULATION REACTIONS CATALYZED BY A TRYPTOPHAN-DERIVED OXAZABOROLIDINE [J].

COREY, EJ ;

CYWIN, CL ;

ROPER, TD .

TETRAHEDRON LETTERS, 1992, 33 (46) :6907-6910

[6]

Danishefsky S. J., 1986, ALDRICHIM ACTA, V19, P59

[7] TOTALLY SYNTHETIC ROUTES TO THE HIGHER MONOSACCHARIDES [J].

DANISHEFSKY, SJ ;

DENINNO, MP .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (01) :15-23

[8] ON THE SCOPE, MECHANISM, AND STEREOCHEMISTRY OF THE LEWIS ACID-CATALYZED CYCLOCONDENSATION OF ACTIVATED DIENES WITH ALDEHYDES - AN APPLICATION TO THE ERYTHRONOLIDE PROBLEM [J].

DANISHEFSKY, SJ ;

LARSON, E ;

ASKIN, D ;

KATO, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) :1246-1255

[9]

DANISHEFSKY SJ, 1989, CHEMTRACTS, P273

[10] ASYMMETRIC HETERO-DIELS-ALDER REACTION CATALYZED BY STABLE AND EASILY PREPARED CAB CATALYSTS [J].

GAO, QZ ;

MARUYAMA, T ;

MOURI, M ;

YAMAMOTO, H .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :1951-1952

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