Efficient Synthesis of 3-Chloromethyl-2(5H)-furanones and 3-Chloromethyl-5,6-dihydropyran-2-ones via the PdCl2-Catalyzed Chlorocyclocarbonylation of 2,3-or 3,4-Allenols

被引：37

作者：

Cheng, Xin ^{[1
]}

Jiang, Xuefeng ^{[1
]}

Yu, Yihua ^{[2
]}

Ma, Shengming ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

[2] E China Normal Univ, Dept Phys, Shanghai Key Lab Funct Magnet Resonance Imaging, Shanghai 200062, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 22期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1021/jo8015677

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and efficient methodology involving PdCl2-catalyzed chlorocyclocarbonylation of 2,3- or 3,4-allenols with CuCl2 for the synthesis of 3-chloromethyl-2(5H)-furanones and 3-chloromethyl-5,6-dihydropyran-2-ones was developed. This reaction proceeded in a highly regioselective manner, i.e., the chlorine atom was introduced to the terminal position of the allene moiety while the lactone linkage was formed between the center carbon atom of the allene moiety and the hydroxyl oxygen, which was established by the X-ray single crystal diffraction study of gamma-lactone 3p. The highly optically active 3-chloromethyl-2(5H)-furanones could be easily prepared from the readily available optically active 2,3-allenols. A mechanism for this reaction was proposed.

引用

页码：8960 / 8965

页数：6

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