期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 77, 期 14, 页码 6327-6331出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo300806y
关键词
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资金
- Consolider-Ingenio [CSD2007-00006]
- Spanish Ministerio de Educacion
Double addition (1,2-1,4) of vinyl magnesium bromide to squaric acid derivatives allows the preparation of polyoxygenated cyclopentenones (8) in a one-pot procedure. The reaction occurs through the intermediate formation of octatetraenes (6). Protonation of this latter intermediate at -78 degrees C with TFE occurs selectively at the vinyl CH2 closer to the metallic centers. DFT studies of the cyclization step justify the observed distereoselectivity.
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