PALLADIUM-CATALYZED OXASPIROCYCLIZATIONS

被引：27

作者：

ANDERSSON, PG

NILSSON, YIM

BACKVALL, JE

机构：

[1] Department of Organic Chemistry, University of Uppsala, S-751 21 Uppsala

来源：

TETRAHEDRON | 1994年 / 50卷 / 02期

关键词：

D O I：

10.1016/S0040-4020(01)80776-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed oxidation of 1-(3-hydroxyalkyl) and 1-(4-hydroxyalkyl)-1,3-cycloalkadienes results in a stereocontrolled oxaspirocyclization. The reaction proceed via a spirocyclic (pi-allyl)palladium intermediate, which is attacked by an acetate or a chloride nucleophile leading to an overall 1,4-addition across the diene. The intermediate (pi-allyl) palladium complex was independently prepared and characterized The stereochemistry of the 1,4-addition can be controlled to give either cis or trans 1,4-addition across the double bonds. The oxaspirocyclization was applied to the total synthesis of theaspirone.

引用

页码：559 / 572

页数：14

共 20 条

[1] PALLADIUM-CATALYZED TANDEM CYCLIZATION OF 4,6-DIENE AND 5,7-DIENE AMIDES - A NEW ROUTE TOWARD THE PYRROLIZIDINE AND INDOLIZIDINE ALKALOIDS [J].