Tin(IV) Chloride Catalyzed Cycloaddition Reactions between 3-Ethoxycyclobutanones and Allylsilanes

Formal [4 + 2] cycloaddition between various 3-ethoxycyclobutanones and allyltrialkylsilanes proceeded to give 3-ethoxy-5-[(trialkylsilyl)methyl]cyclohexan-1-ones by catalysis with tin(VI) chloride. The use of allyl-tert-butyldiphenylsilane induced 1,5-hydride transfer, which gave 2-[3-(tert-butyldi...

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Bibliographic Details
Published in:Organic letters 2009-09, Vol.11 (17), p.3822-3825
Main Authors: Matsuo, Jun-ichi, Sasaki, Shun, Hoshikawa, Takaya, Ishibashi, Hiroyuki
Format: Article
Language:English
Subjects:
Allyl Compounds - chemistry
Catalysis
Cyclization
Cyclobutanes - chemistry
Molecular Structure
Pyrones - chemical synthesis
Pyrones - chemistry
Silanes - chemistry
Stereoisomerism
Tin Compounds - chemistry
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Summary:Formal [4 + 2] cycloaddition between various 3-ethoxycyclobutanones and allyltrialkylsilanes proceeded to give 3-ethoxy-5-[(trialkylsilyl)methyl]cyclohexan-1-ones by catalysis with tin(VI) chloride. The use of allyl-tert-butyldiphenylsilane induced 1,5-hydride transfer, which gave 2-[3-(tert-butyldiphenylsilyl)propyl]-6-methyltetrahydro-4-pyrones.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol901329c