Metal-catalyzed asymmetric hetero-Diels-Alder reactions of unactivated dienes with glyoxylates

被引：43

作者：

Johannsen, M ^{[1
]}

Yao, SL ^{[1
]}

Graven, A ^{[1
]}

Jorgensen, KA ^{[1
]}

机构：

[1] Aarhus Univ, Dept Chem, Ctr Met Catalyzed React, DK-8000 Aarhus C, Denmark

来源：

PURE AND APPLIED CHEMISTRY | 1998年 / 70卷 / 05期

关键词：

D O I：

10.1351/pac199870051117

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The development of a catalytic asymmetric hetero-Diels-Alder methodology for the reaction of unactivated dienes with glyoxylates is presented. Several different asymmetric catalysts can be used, but copper-bisoxazolines and aluminium-BINOL give the highest yield, and the best chemo- and enantioselectivities. The reaction course is dependent on several factors such as the solvent and the anions coordinated to the catalyst. The scope of the reaction is outlined by the total synthesis of a natural occurring actinidiolide.

引用

页码：1117 / 1122

页数：6

共 23 条

[11] Importance of chiral activators in the asymmetric catalysis of Diels-Alder reactions by chiral titanium(IV) complexes [J].

Matsukawa, S ;

Mikami, K .

TETRAHEDRON-ASYMMETRY, 1997, 8 (06) :815-816

[12] ASYMMETRIC ENE REACTIONS IN ORGANIC-SYNTHESIS [J].

MIKAMI, K ;

SHIMIZU, M .

CHEMICAL REVIEWS, 1992, 92 (05) :1021-1050

[13] ASYMMETRIC CATALYSIS OF DIELS-ALDER CYCLOADDITIONS BY AN MS-FREE BINAPHTHOL-TITANIUM COMPLEX - DRAMATIC EFFECT OF MS, LINEAR VS POSITIVE NONLINEAR RELATIONSHIP, AND SYNTHETIC APPLICATIONS [J].

MIKAMI, K ;

MOTOYAMA, Y ;

TERADA, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :2812-2820

[14] ASYMMETRIC CATALYSIS OF DIELS-ALDER CYCLOADDITION BY A BETA-AMINO ALCOHOL DERIVED BORON COMPLEX - REASONABLE TRANSITION-STATE ASSEMBLY FOR ONE-DIRECTIONAL DIENE APPROACH [J].

MOTOYAMA, Y ;

MIKAMI, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (13) :1563-1564

[15]

NARASAKA K, 1991, SYNTHESIS-STUTTGART, P1

[16] ASYMMETRIC DIELS-ALDER REACTION - COMPARISON OF MENTHOXYALUMINUM AND LANTHANIDE CHIRAL CATALYSTS [J].

QUIMPERE, M ;

JANKOWSKI, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (09) :676-677

[17] THE QUEEN RECOGNITION PHEROMONE OF SOLENOPSIS-INVICTA, PREPARATION OF (E)-6-(1-PENTENYL)-2H-PYRAN-2-ONE [J].

ROCCA, JR ;

TUMLINSON, JH ;

GLANCEY, BM ;

LOFGREN, CS .

TETRAHEDRON LETTERS, 1983, 24 (18) :1889-1892

[18] PERISELECTIVE AND ENANTIOSELECTIVE CARBONYL-ENE REACTION OF ISOPRENE WITH FLUOROALKYL GLYOXYLATE CATALYZED BY MODIFIED BINAPHTHOL-TITANIUM COMPLEX - ASYMMETRIC CATALYTIC SYNTHESIS OF ENANTIOMERICALLY PURE IPSDIENOL [J].

TERADA, M ;

MIKAMI, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (23) :2391-2392

[19] ENANTIOSELECTIVE HETERO-DIELS-ALDER REACTION WITH GLYOXYLATE CATALYZED BY CHIRAL TITANIUM COMPLEX - ASYMMETRIC-SYNTHESIS OF THE LACTONE PORTION OF MEVINOLIN AND COMPACTIN [J].

TERADA, M ;

MIKAMI, K ;

NAKAI, T .

TETRAHEDRON LETTERS, 1991, 32 (07) :935-938

[20] ASYMMETRIC HETERO-DIELS-ALDER REACTIONS CATALYZED BY NOVEL CHIRAL VANADIUM(IV) BIS(1,3-DIKETONATO) COMPLEXES [J].

TOGNI, A .

ORGANOMETALLICS, 1990, 9 (12) :3106-3113

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