TRICYCLO[5.2.1.0(2,6)]DECADIENONE EPOXIDES - RIGID, HIGHLY CONGESTED ALPHA,BETA-EPOXYCYCLOPENTANONES WITH DISTINCTIVE CHEMICAL BEHAVIOR

被引：9

作者：

LANGE, JHM ^{[1
]}

SOMMERDIJK, NAJM ^{[1
]}

DOLS, PPMA ^{[1
]}

ARNOUTS, EG ^{[1
]}

KLUNDER, AJH ^{[1
]}

ZWANENBURG, B ^{[1
]}

机构：

[1] CATHOLIC UNIV NIJMEGEN,DEPT ORGAN CHEM,6525 ED NIJMEGEN,NETHERLANDS

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 26期

关键词：

D O I：

10.1016/0040-4039(91)80707-D

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tricyclodecadienone epoxides 5 do not form an enolate on treatment with lithium diisopropyl amide, but instead undergo an unusual stereoselective beta-hydride transfer leading to alcohols 6. The same type of epoxy endo-alcohol was obtained from parent epoxy ketone 5 on reaction with metal hydrides and organolithium reagents. These alcohols readily undergo an intramolecular epoxide migration by a Payne-type rearrangement, to give endo-epoxides 9.

引用

页码：3127 / 3130

页数：4

共 24 条

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[8] ENZYMATIC OPTICAL RESOLUTION AND FLASH VACUUM THERMOLYSIS IN CONCERT FOR THE SYNTHESIS OF OPTICALLY-ACTIVE CYCLOPENTENONES
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