STEREOSELECTIVE CONVERGENT SYNTHESIS OF HYDROAZULENES VIA AN INTERMOLECULAR CYCLOPROPANATION COPE REARRANGEMENT

被引：34

作者：

CANTRELL, WR ^{[1
]}

DAVIES, HML ^{[1
]}

机构：

[1] WAKE FOREST UNIV,DEPT CHEM,WINSTON SALEM,NC 27109

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 02期

关键词：

D O I：

10.1021/jo00002a044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium(II) acetate catalyzed decomposition of vinyldiazomethane 1 to a vinylcarbenoid intermediate in the presence of oxygenated dienes led to the direct formation of hydroazulenes 7, 13, and 15-19. The 3 + 4 annulation proceeds by a tandem cyclopropanation/Cope rearrangement sequence. The cyclopropanation is highly stereoselective, favoring the formation of cis-divinylcyclopropanes. Due to the boat transition state required for the Cope rearrangement of cis-divinylcyclopropanes, the hydroazulenes are formed with predictable stereocontrol.

引用

页码：723 / 727

页数：5

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