高立体选择性恶唑硼烷离子催化的烷基芳基酮与三甲基硅基重氮甲烷反应合成(Z)-硅基烯醇醚。
Highly stereoselective oxazaborolidinium ion catalyzed synthesis of (Z)-silyl enol ethers from alkyl aryl ketones and trimethylsilyldiazomethane.
机构信息
Department of Chemistry, Sungkyunkwan University , Suwon, 440-746, Korea.
出版信息
Org Lett. 2014 Apr 18;16(8):2077-9. doi: 10.1021/ol500174q. Epub 2014 Mar 26.
PMID:24670001
Abstract
Highly stereoselective (Z)-silyl enol ethers were prepared from alkyl aryl ketones and trimethylsilyldiazomethane (TMSD) using an oxazaborolidinium ion catalyst. In addition, ring-expanded silyl enol ethers were successfully constructed from cyclic ketones. Their synthetic utilities were shown by sequential Mukaiyama aldol and [2 + 2]-cycloaddition reactions.
摘要
高立体选择性的（Z）-硅基烯醇醚可由芳基烷基酮和三甲基硅基重氮甲烷（TMSD）在噁唑硼烷离子催化剂的作用下制备。此外，环状酮也可成功构建环扩大的硅基烯醇醚。通过连续的 Mukaiyama 羟醛缩合和[2+2]-环加成反应，展示了它们的合成实用性。
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