Stereoselective synthesis of highly functionalized 1,5-oxa-bridged cyclooctenes via a 3-oxidopyrylium-cyclocypropene acetal cycloaddition

被引：24

作者：

Delgado, A

Castedo, L

Mascareñas, JL ^{[1
]}

机构：

[1] Univ Santiago de Compostela, Dept Quim Organ, Santiago De Compostela 15782, Spain

[2] Univ Santiago de Compostela, CSIC, Unidad Asociada, Santiago De Compostela 15782, Spain

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 18期

关键词：

D O I：

10.1021/ol0263954

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A [5C+2C] oxidopyrylium-cyclopropenone acetal cycloaddition followed by ring opening of the cyclopropane unit of the resulting adduct leads to highly substituted 1,5-oxa-bridged cyclooctenes containing up to four stereocenters. The protocol formally constitutes a [5C+3C] annulation process.

引用

页码：3091 / 3094

页数：4

共 24 条

[1]

Boger D. L., 1990, ADV CYCLOADDITION, V2, P147

[2] THERMAL-REACTIONS OF CYCLOPROPENONE KETALS - KEY MECHANISTIC FEATURES AND SCOPE OF THE CYCLOADDITION REACTIONS OF DELOCALIZED SINGLET VINYLCARBENES - 3-CARBON 1,1-DIPOLES 1,3-DIPOLES [J].