N-杂环卡宾引发的α-酰基乙烯基阴离子反应活性：α-羟基炔丙基硅烷与醛的加成反应
N-heterocyclic carbene-initiated alpha-acylvinyl anion reactivity: additions of alpha-hydroxypropargylsilanes to aldehydes.
作者信息
Reynolds Troy E, Stern Charlotte A, Scheidt Karl A
机构信息
Department of Chemistry, Northwestern University, Evanston, Illinois 60208, USA.
出版信息
Org Lett. 2007 Jun 21;9(13):2581-4. doi: 10.1021/ol0710515. Epub 2007 Jun 1.
Abstract
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 (R1) can be accommodated in moderate to excellent yields with a high degree of control over the resulting alkene.
摘要
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。对于这类化合物，该策略是标准的森田-贝利斯-希尔曼（MBH）方法的一种高效替代方法。与MBH反应不同，产物β位（R1）的不同取代基可以以中等至优异的产率得到，并且对所得烯烃具有高度的可控性。
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