Metal-catalyzed Asymmetric Hetero-Diels-Alder Reactions of                Unactivated Dienes with Glyoxylates.

Mogens Johannsen; Sulan Yao; Anette Graven

doi:10.1351/pac199870051117

Metal-catalyzed Asymmetric Hetero-Diels-Alder Reactions of Unactivated Dienes with Glyoxylates.

Mogens Johannsen
, Sulan Yao
, Anette Graven

Aarhus University

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

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.

Original language	English
Journal	Pure and Applied Chemistry
Volume	70
Issue number	5
Pages (from-to)	1117-1122
ISSN	0033-4545
DOIs	https://doi.org/10.1351/pac199870051117
Publication status	Published - 1998

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title = "Metal-catalyzed Asymmetric Hetero-Diels-Alder Reactions of Unactivated Dienes with Glyoxylates.",

abstract = "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. ",

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year = "1998",

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T1 - Metal-catalyzed Asymmetric Hetero-Diels-Alder Reactions of Unactivated Dienes with Glyoxylates.

AU - Johannsen, Mogens

AU - Yao, Sulan

AU - Graven, Anette

PY - 1998

Y1 - 1998

N2 - 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.

AB - 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.

U2 - 10.1351/pac199870051117

DO - 10.1351/pac199870051117

M3 - Journal article

SN - 0033-4545

VL - 70

SP - 1117

EP - 1122

JO - Pure and Applied Chemistry

JF - Pure and Applied Chemistry

IS - 5

ER -

Metal-catalyzed Asymmetric Hetero-Diels-Alder Reactions of Unactivated Dienes with Glyoxylates.

Abstract

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