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硼烷催化内炔酰胺的选择性硅氢化反应生成β-硅基（Z）-烯酰胺。

Borane-Catalyzed Selective Hydrosilylation of Internal Ynamides Leading to β-Silyl (Z)-Enamides.

机构信息

Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST) , Daejeon 34141, Korea.

Center for Catalytic Hydrocarbon Functionalization, Institute for Basic Science (IBS) , Daejeon 34141, Korea.

出版信息

Org Lett. 2017 Jan 6;19(1):190-193. doi: 10.1021/acs.orglett.6b03485. Epub 2016 Dec 12.

DOI:10.1021/acs.orglett.6b03485
PMID:27936799
Abstract

We have developed a borane-catalyzed regio- and stereoselective hydrosilylation of internal ynamides for the first time. The scope of ynamide substrates and silane reactants was broad under mild reaction conditions, affording synthetically versatile β-silyl (Z)-enamide products. The observed stereoselectivity was reasoned to be due to the β-silicon effect on a postulated ketene iminium intermediate.

摘要

我们首次开发了硼烷催化的内炔酰胺的区域和立体选择性氢化硅烷化反应。在温和的反应条件下，炔酰胺底物和硅烷反应物的范围很广，得到了具有合成多功能性的β-硅基（Z）-烯酰胺产物。观察到的立体选择性被认为是由于β-硅对假定的烯酮亚胺中间体的影响。

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