通过手性二醇的催化对映选择性硅烷化反应实现区域发散反应。萨宾呋喃酮 A 的合成。
Regiodivergent reactions through catalytic enantioselective silylation of chiral diols. Synthesis of sapinofuranone A.
机构信息
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
出版信息
Org Lett. 2011 Aug 5;13(15):3778-81. doi: 10.1021/ol2010819. Epub 2011 Jun 28.
Abstract
Through the use of an amino acid based imidazole catalyst, a regiodivergent silylation of chiral diols in cases where there is not a significant steric and electronic difference between the regioisotopic hydroxyl groups has been developed. This transformation allows for the conversion of racemic diols into regioisomeric, enantiomerically enriched, monosilylated products. The utility of this process is highlighted in the efficient enantioselective preparation of a useful synthetic intermediate and the natural product, sapinofuranone A.
摘要
通过使用氨基酸基咪唑催化剂，开发了一种在区域异构体羟基之间没有显著的空间和电子差异的情况下，手性二醇的区域发散性硅烷化反应。这种转化允许将外消旋二醇转化为区域异构体、对映体富集、单硅烷化产物。该过程的实用性在有效对映选择性制备有用的合成中间体和天然产物 sapinofuranone A 中得到了突出体现。
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