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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
其他题名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
Cheng X(程鑫); Jiang XF(姜雪峰); Yu YH(余亦华); Ma SM(麻生明)
2008
发表期刊J. Org. Chem.
ISSN0022-3263
卷号73期号:22页码:8960-8965
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.
学科领域金属有机化学
部门归属上海有机所; 华东师范大学
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收录类别SCI
语种英语
WOS记录号WOS:000260923000030
引用统计
被引频次:33[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/12146
专题金属有机化学国家重点实验室
通讯作者Ma SM(麻生明)
推荐引用方式
GB/T 7714
Cheng X,Jiang XF,Yu YH,et al. 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[J]. J. Org. Chem.,2008,73(22):8960-8965.
APA 程鑫,姜雪峰,余亦华,&麻生明.(2008).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.J. Org. Chem.,73(22),8960-8965.
MLA 程鑫,et al."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".J. Org. Chem. 73.22(2008):8960-8965.
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