Synthesis of Bicyclic Ethers by a Gold/Palladium/Gold-Catalyzed Cyclization/Cross Coupling Sequence

被引：40

作者：

Gockel, Birgit ^{[1
]}

Krause, Norbert ^{[1
]}

机构：

[1] Dortmund Univ Technol, D-44227 Dortmund, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 02期

关键词：

Allenes; Cycloisomerization; Gold; Homogeneous catalysis; Oxygen heterocycles; 2,3 WITTIG REARRANGEMENT; STEREOSELECTIVE-SYNTHESIS; GOLDEN OPPORTUNITIES; ALPHA-HYDROXYALLENES; N-IODOSUCCINIMIDE; CYCLOISOMERIZATION; ALLENES; ALKYNES; ENYNES; 2,5-DIHYDROFURANS;

D O I：

10.1002/ejoc.200901010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective gold-catalyzed 6-endo cyclization. of various beta-hydroxyallenes in the presence of N-iodosuccinimide affords iodinated dihydropyrans in good yield. Subsequent functionalization by palladium-catalyzed cross coupling opens an access to alpha-hydroxyallenes that are converted in a second gold-catalyzed cyclization into furopyrans which occur in various natural products.

引用

页码：311 / 316

页数：6

共 91 条

[1] STEREOSELECTIVE ALLYLIC TRANSPOSITION BY MEANS OF ALLYLIC N-PENTENYL ETHERS [J].