Author/Authors :
Honda، نويسنده , , Mitsunori and Mita، نويسنده , , Takahito and Nishizawa، نويسنده , , Toshiaki and Sano، نويسنده , , Toru and Segi، نويسنده , , Masahito and Nakajima، نويسنده , , Tadashi، نويسنده ,
Abstract :
Treatment of 1-silylcyclopropylmethanols with TsOH in methanol gives different homoallyl ethers depending upon the configuration of substituents on cyclopropane ring and the kinds of substituents on carbinyl carbon. Especially, the reaction of cyclopropylmethanols having no substituents on the same side with silyl group on cyclopropane ring proceeds to give the corresponding E-homoallyl ethers with high stereoselectivity. The following protiodesilylation of resulting homoallyl ethers proceeds with retention of configuration.
Keywords :
Cyclopropylmethanol , Homoallylic rearrangement , Trimethylsilyl group , Protiodesilylation
