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

[1]

BOGER DL, 1987, HETERO DIELSALDER ME

[2] 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

[3] 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

[4]

GRAVEN A, 1996, J CHEM SOC CHEM COMM, P2373

[5] Solvent vs. counterion acceleration of enantioselective carbo and hetero Diels-Alder reactions [J].

Johannsen, M ;

Jorgensen, KA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (06) :1183-1185

[6] Solvent effects in asymmetric hetero Diels-Alder and ene reactions [J].

Johannsen, M ;

Jorgensen, KA .

TETRAHEDRON, 1996, 52 (21) :7321-7328

[7] ASYMMETRIC HETERO-DIELS-ALDER REACTIONS AND ENE REACTIONS CATALYZED BY CHIRAL COPPER(II) COMPLEXES [J].

JOHANNSEN, M ;

JORGENSEN, KA .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5757-5762

[8]

KAGAN HB, 1992, CHEM REV, V92, P1008

[9] CATALYTIC ENANTIOSELECTIVE SYNTHESIS OF DIHYDROPYRONES VIA FORMAL HETERO-DIELS-ALDER REACTIONS OF DANISHEFSKYS DIENE WITH ALDEHYDES [J].

KECK, GE ;

LI, XY ;

KRISHNAMURTHY, D .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19) :5998-5999

[10] ASYMMETRIC HETERO-DIELS-ALDER REACTION CATALYZED BY CHIRAL ORGANO-ALUMINUM REAGENT [J].

MARUOKA, K ;

ITOH, T ;

SHIRASAKA, T ;

YAMAMOTO, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (01) :310-312

← 1 2 3 →