Acid-catalyzed intramolecular addition of a carboxy group to vinylsilanes
详细信息 查看全文
- 作者：Miura ; Katsukiyo ; Hayashida ; Joji ; Takahashi ; Tatsuyuki ; Nishikori ; Hisashi ; Hosomi ; Akira
- 关键词：Acid Catalyst ; Cyclization ; Vinylsilane ; γ ; -lactone
- 刊名：Journal of Organometallic Chemistry
- 出版年：2003
- 出版时间：November 21, 2003
- 年：2003
- 卷：686
- 期：1-2
- 页码：242-250
- 全文大小：284 K
文摘
In the presence of a catalytic amount of TsOH·H2O or TiCl4, 5-silyl-4-pentenoic acids (1), namely vinylsilanes with a carboxy group, were smoothly cyclized to γ-lactones in good to high yields. The difference in the geometry of the carbon
carbon double-bond did not affect the reaction rate. The TiCl4-catalyzed cyclization of the substrates bearing a phenyl or alkyl group at the homoallylic position showed moderate cis-selectivity, while introduction of a substituent into the allylic position led to high trans-selectivity.
carbon double-bond did not affect the reaction rate. The TiCl4-catalyzed cyclization of the substrates bearing a phenyl or alkyl group at the homoallylic position showed moderate cis-selectivity, while introduction of a substituent into the allylic position led to high trans-selectivity.