Novel Skeleton Transformation Reaction of α‑Pyrone Derivatives to Spirobicyclo[3.1.0]hexane Derivatives Using Dimethylsulfoxonium Methylide

By applying a skeleton transformation reaction using dimethylsulfoxonium methylide, a novel reaction was identified by which 5,6,7,8-tetrahydrocoumarin with the electron-withdrawing group at C3 was led to the spirobicyclo[3.1.0]hexane-cyclohexane derivative. Moreover, by establishing the scope of th...

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Bibliographic Details
Published in:Organic letters 2012-12, Vol.14 (23), p.6048-6051
Main Authors: Miura, Takuya, Yadav, Navnath Dnyanoba, Iwasaki, Hiroki, Ozeki, Minoru, Kojima, Naoto, Yamashita, Masayuki
Format: Article
Language:English
Subjects:
Bridged Bicyclo Compounds - chemical synthesis
Bridged Bicyclo Compounds - chemistry
Hexanes - chemistry
Molecular Structure
Pyrones - chemistry
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
Sulfonium Compounds - chemistry
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Summary:By applying a skeleton transformation reaction using dimethylsulfoxonium methylide, a novel reaction was identified by which 5,6,7,8-tetrahydrocoumarin with the electron-withdrawing group at C3 was led to the spirobicyclo[3.1.0]hexane-cyclohexane derivative. Moreover, by establishing the scope of this reaction, it was confirmed that it is possible to apply this reaction to not only ring-fused α-pyrone derivatives but also alkyl-chain-substituted α-pyrone derivatives in moderate to good yields.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol302942m