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Halonium-initiated C - O bond formation via umpolung of α-carbon to the carbonyl: Efficient access to 5-amino-3(2 H)-furanones

Organic Letters, ISSN: 1523-7060, Vol: 14, Issue: 3, Page: 712-715
2012
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Article Description

Highly efficient C - O bond formation has been developed via carboxylic acid catalyzed reaction of 1-acetylcyclopropanecarboxamides with N-halosuccinimide (NXS), which provides strategically novel and atom-economic access to biologically important 5-amino-3(2H)-furanones. The mechanism of halonium-initiated tandem oxa-cyclization and ring opening of cyclopropane was proposed. A variety of nucleophiles were found to open the cyclopropane. © 2012 American Chemical Society.

Bibliographic Details

Wei, Ying; Lin, Shaoxia; Xue, Hongxun; Liang, Fushun; Zhao, Baozhong

American Chemical Society (ACS)

Biochemistry, Genetics and Molecular Biology; Chemistry

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