Yadav Veejendra K, Balamurugan Rengarajan
Department of Chemistry, Indian Institute of Technology, Kanpur 208 016, India.
Org Lett. 2003 Nov 13;5(23):4281-4. doi: 10.1021/ol035481g.
[reaction: see text] Vicinally substituted trimethylsilylmethyl cyclopropyl ketones undergo facile desilylative ring opening with Lewis acids under mild conditions. The enolates, thus generated, undergo aldol addition with aldehydes and ketones. The diastereoselectivity of the reaction with aldehydes depends on the nature of the Lewis acid used. The resulting aldol product is easily converted into a substituted tetrahydrofuran derivative.
[反应：见正文] 邻位取代的三甲基硅基甲基环丙基酮在温和条件下与路易斯酸发生容易的脱硅基开环反应。由此生成的烯醇盐与醛和酮发生羟醛加成反应。与醛反应的非对映选择性取决于所用路易斯酸的性质。所得的羟醛产物可容易地转化为取代的四氢呋喃衍生物。
