N-heterocyclic carbene-initiated α-acylvinyl anion reactivity:: Additions of α-hydroxypropargylsilanes to aldehydes
N-heterocyclic carbene-initiated α-acylvinyl anion reactivity:: Additions of α-hydroxypropargylsilanes to aldehydes
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DOI：
10.1021/ol0710515
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发表时间：
2007-06-21
期刊：
影响因子：
5.2
通讯作者：
Scheidt, Karl A.
中科院分区：
文献类型：
--
作者：
Reynolds, Troy E.;Stern, Charlotte A.;Scheidt, Karl A.
通过N-杂环卡宾引发的α-羟基炔丙基硅烷与醛的加成反应制备高度取代的α，β-不饱和酮。这种策略作为一种高效的替代标准的Morita-Baylis-Hillman（MBH）的方法，这些类型的化合物。与MBH反应相反，在产物（R-1）的β-位上的不同取代可以以中等至优异的产率进行调节，并且对所得烯烃具有高度的控制。
Highly substituted alpha,beta-unsaturated ketones are prepared by the N-heterocyclic carbene-initiated addition of alpha-hydroxypropargylsilanes to aldehydes. This strategy serves as a highly efficient alternative to the standard Morita-Baylis-Hillman (MBH) approaches for these types of compounds. In contrast to the MBH reaction, different substitution in the beta-position of the product (R-1) can be accommodated in moderate to excellent yields with a high degree of control over the resulting alkene.