Synthesis of α,β-unsaturated γ-lactones via photooxygenation of 2,3-dihydrofurans followed by ferrous ion-catalyzed gem-dehydration

被引：16

作者：

Chen, Yu-Zhe ^{[1
]}

Wu, Li-Zhu ^{[1
]}

Peng, Ming-Li ^{[1
]}

Zhang, Dong ^{[1
]}

Zhang, Li-Ping ^{[1
]}

Tung, Chen-Ho ^{[1
]}

机构：

[1] Chinese Acad Sci, Tech Inst Phys & Chem, Beijing 100080, Peoples R China

来源：

TETRAHEDRON | 2006年 / 62卷 / 46期

基金：

中国国家自然科学基金;

关键词：

alpha; beta-unsaturated gamma-lactones; photooxy.genation of 2,3-dihydrofurans; ferrous ion-catalyzed gem-dehydration of hydroperoxides;

D O I：

10.1016/j.tet.2006.08.085

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several alkyl and aryl substituted 2,3-dihydrofurans la-le were synthesized and their reactions with singlet oxygen were investigated. Photooxygenation of la-le in carbon tetrachloride at ambient temperature exclusively yields allylic hydroperoxides 4a-4e. Treatment of these hydroperoxides with aqueous ferrous sulfate solution affords the corresponding alpha,beta-unsaturated gamma-lactones 6a-6e with high yields. This work provides an efficient route to the preparation of butenolide moiety, an important functionality in the structures of many natural products that exhibit biological properties. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：10688 / 10693

页数：6

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