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Paper | Special issue | Vol 67, No. 1, 2006, pp.369-374
Published online, 13th September, 2005
DOI: 10.3987/COM-05-S(T)60
Stereoselective Synthesis of Tetrahydrofuran by Diasteroselective [3+2] Cycloaddition Reaction of Chiral Allylsilane with α-Keto Ester

Takahiko Akiyama,* Shinya Funaki, and Kohei Fuchibe

*Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1, Mejiro, Toshima-ku, Tokyo 171-8588, Japan


Lewis acid mediated [3+2] cycloaddition reaction of chiral allylsilane, bearing a stereogenic center on the silyl substituents, with ±-keto ester gave silyl-substituted tetrahydrofurans with good to high stereoselectivity.