Synthesis of 1,2,4-trioxepanes and 1,2,4-trioxocanes via photooxygenation of homoallylic alcohols

被引：30

作者：

Singh, Chandan ^{[1
]}

Pandey, Shilpi ^{[1
]}

Saxena, Gunjan ^{[1
]}

Srivastava, Nisha ^{[1
]}

Sharma, Malvika ^{[1
]}

机构：

[1] Cent Drug Res Inst, Div Med & Proc Chem, Lucknow 226001, Uttar Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 24期

关键词：

D O I：

10.1021/jo061414z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Homoallylic alcohols 4a-d, easily accessible in two steps from cyclopropyl methyl ketone, underwent a highly regioselective reaction with singlet oxygen to yield gamma-hydroxyhydroperoxides 5a-d in 57-72% yield. Acid-catalyzed reaction of 5a-d with acetone, cyclopentanone, and cyclohexanone furnished 1,2,4-trioxepanes 8a-d, 9a-d, and 10a-d in good yields. Homoallylic alcohol 12 also underwent a highly regioselective photooxygenation to yield delta-hydroxyhydroperoxide 13 in 67% yield, which on reaction with acetone, cyclopentanone, and cyclohexanone, furnished 1,2,4-trioxocanes 16-18 in 41-55% yield.

引用

页码：9057 / 9061

页数：5

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