期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 73, 期 22, 页码 8960-8965出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo8015677
关键词
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资金
- Major State Basic Research Development Program [2006CB806105]
- National Natural Science Foundation of China [20732005, 20423001]
- Shanghai Municipal Committee of Science and Technology
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.
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