DIANANE-CrIII-salen complexes as highly enantioselective catalysts for hetero-Diels-Alder reactions of aldehydes with dienes

被引：27

作者：

Berkessel, Albrecht ^{[1
]}

Vogl, Nadine ^{[1
]}

机构：

[1] Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 2006卷 / 22期

关键词：

asymmetric catalysis; chromium; hetero-Diels-Alder reaction; homogeneous catalysis;

D O I：

10.1002/ejoc.200600359

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new type of chromium-salen complex bearing DIANANE (endo,endo-2,5-diaminonorbornane) as chiral backbone has been synthesized and applied to the hetero-Diels-Alder reaction of Danishefsky's diene with various aldehydes. The reactions afford the corresponding 2-substituted 2,3-dihydro-4H-pyran-4-ones in high yields and enantioselectivities (up to 96 % ee). The effect of different counteranions of the complex on reactivity as well as enantioselectivity has been investigated. Besides Danishefsky's diene, reaction of the less reactive 1-methoxybutadiene with benzaldehyde and ethyl glyoxylate can be effected by the chromium catalysts as well. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).

引用

页码：5029 / 5035

页数：7

共 71 条

[1] Asymmetric hetero Diels-Alder reaction using chiral cationic metallosalen complexes as catalysts [J].

Aikawa, K ;

Irie, R ;

Katsuki, T .

TETRAHEDRON, 2001, 57 (05) :845-851

[2] A new dirhodium(II) carboxamidate complex as a chiral lewis acid catalyst for enantioselective hetero-Diels-Alder reactions [J].

Anada, M ;

Washio, T ;

Shimada, N ;

Kitagaki, S ;

Nakajima, M ;

Shiro, M ;

Hashimoto, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (20) :2665-2668

[3]

Anada M., 2004, ANGEW CHEM, V116, P2719

[4] A novel catalytic and highly enantioselective approach for the synthesis of optically active carbohydrate derivatives [J].

Audrain, H ;

Thorhauge, J ;

Hazell, RG ;

Jorgensen, KA .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4487-4497

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

BEDNARSKI, M ;

MARING, C ;

DANISHEFSKY, S .

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

[6] ON THE INTERACTIVITY OF CHIRAL AUXILIARIES WITH CHIRAL CATALYSTS IN THE HETERO DIELS-ALDER REACTION - A NEW ROUTE TO L-GLYCOLIPIDS [J].

BEDNARSKI, M ;

DANISHEFSKY, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (23) :6968-6969

[7]

BERKESSEL, UNPUB

[8] Chiral chromium(III) porphyrins as highly enantioselective catalysts for hetero-Diels-Alder reactions between aldehydes and dienes [J].

Berkessel, A ;

Ertürk, E ;

Laporte, C .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (1-2) :223-228

[9] Enantioselective synthesis of DIANANE, a novel C2-symmetric chiral diamine for asymmetric catalysis [J].

Berkessel, A ;

Schröder, M ;

Sklorz, CA ;

Tabanella, S ;

Vogl, N ;

Lex, J ;

Neudörfl, JM .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09) :3050-3056

[10] ON THE ACETOXYLATION OF 2,3-DIHYDRO-4-PYRONES - A CONCISE, FULLY SYNTHETIC ROUTE TO THE GLUCAL STEREOCHEMICAL SERIES [J].

DANISHEFSKY, S ;

BEDNARSKI, M .

TETRAHEDRON LETTERS, 1985, 26 (29) :3411-3412

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