Enantioselective rare-earth catalyzed quinone Diels-Alder reactions

被引：80

作者：

Evans, DA ^{[1
]}

Wu, J ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 34期

关键词：

D O I：

10.1021/ja0367602

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly enantioselective, quinone Diels-Alder reaction catalyzed by chiral samarium and gadolinium pyridyl-bis(oxazoline) (pybox) complexes has been developed. The reaction scope has been extended to include three quinones and five dienes, all of which exclusively provide the expected endo product in excellent yields and enantioselectivities. Copyright © 2003 American Chemical Society.

引用

页码：10162 / 10163

页数：2

共 22 条

[1] Catalytic enantioselective Diels-Alder reactions of 1,4-quinone monoketals [J].

Breuning, M ;

Corey, EJ .

ORGANIC LETTERS, 2001, 3 (10) :1559-1562

[2] Use of bis(oxazoline)-metal complexes as chiral catalysts for asymmetric-Diels-Alder reactions using 2-acetyl-1,4-naphthoquinone as a dienophile [J].

Brimble, MA ;

McEwan, JF .

TETRAHEDRON-ASYMMETRY, 1997, 8 (24) :4069-4078

[3]

Corey EJ, 2002, ANGEW CHEM INT EDIT, V41, P1650, DOI 10.1002/1521-3773(20020517)41:10<1650::AID-ANIE1650>3.0.CO

[4]

2-B

[5] ASYMMETRIC QUINONE-BASED DIELS-ALDER REACTIONS [J].

ENGLER, TA ;

LETAVIC, MA ;

TAKUSAGAWA, F .

TETRAHEDRON LETTERS, 1992, 33 (45) :6731-6734

[6] FORMATION AND ISOLATION OF ENANTIOMERICALLY PURE PRODUCTS IN QUANTITY FROM DIELS-ALDER REACTIONS OF 1,4-BENZOQUINONES [J].

ENGLER, TA ;

LETAVIC, MA ;

LYNCH, KO ;

TAKUSAGAWA, F .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (05) :1179-1183

[7] NEW ASYMMETRIC DIELS-ALDER CYCLOADDITION REACTIONS - CHIRAL ALPHA,BETA-UNSATURATED CARBOXIMIDES AS PRACTICAL CHIRAL ACRYLATE AND CROTONATE DIENOPHILE SYNTHONS [J].

EVANS, DA ;

CHAPMAN, KT ;

BISAHA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (15) :4261-4263

[8] ASYMMETRIC DIELS-ALDER CYCLO-ADDITION REACTIONS WITH CHIRAL ALPHA, BETA-UNSATURATED N-ACYLOXAZOLIDINONES [J].

EVANS, DA ;

CHAPMAN, KT ;

BISAHA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1238-1256

[9] A general method for the enantioselective synthesis of pantolactone derivatives [J].

Evans, DA ;

Wu, J ;

Masse, CE ;

MacMillan, DWC .

ORGANIC LETTERS, 2002, 4 (20) :3379-3382

[10] C2-symmetric Sc(III)-complexes chiral Lewis acids.: Catalytic enantioselective aldol additions glyoxylate esters [J].

Evans, DA ;

Masse, CE ;

Wu, J .

ORGANIC LETTERS, 2002, 4 (20) :3375-3378

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