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

Authors :: Hiroyuki Ishibashi
Shun Sasaki
Jun-ichi Matsuo
Takaya Hoshikawa
Source :: Organic Letters. 11:3822-3825
Publication Year :: 2009
Publisher :: American Chemical Society (ACS), 2009.
Abstract: 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.

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