期刊
CHEMISTRYOPEN
卷 1, 期 6, 页码 245-250出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/open.201200037
关键词
calculations; cyclizations; hypervalent iodine; oxidations; rearrangements
资金
- European Union (FP7 IIF Marie Curie grant)
- School of Chemistry, Cardiff University, UK
Aromatic substituents migrate in a novel oxidative cyclization mediated by iodine(III) reagents. 4-Arylbut-3-enoic acids are cyclized and rearranged to 4-arylfuran-2(5H)-ones by hypervalent iodine compounds in good to excellent yields under mild reaction conditions. Other ring sizes are also accessible. The mechanism of the reaction is described in detail, and calculations highlight the cationic nature of the intermediates in the rearrangement. The fast access to heavily substituted furanones is used for the synthesis of biologically active derivatives.
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