NHC 催化的 3-羟基色原酮 α,β-不饱和酰基氮杂环丙烷的对映选择性 C2 官能化。
NHC-catalyzed enantioselective C2-functionalization of 3-hydroxychromenones α,β-unsaturated acyl azoliums.
机构信息
Nicolaus Copernicus University in Torun, Faculty of Chemistry, 7 Gagarin Street, 87-100 Toruń, Poland.
出版信息
Chem Commun (Camb). 2021 Sep 30;57(78):9999-10002. doi: 10.1039/d1cc03708k.
PMID:34490868
Abstract
A novel synthetic method for enantioselective C2-functionalization of 3-hydroxychromenones promoted by N-heterocyclic carbenes the formation of α,β-unsaturated acyl azolium intermediates, which occurs with Coates-Claisen rearrangement is established. This synthetic strategy enabled the rapid assembly of enantiomerically enriched δ-hydroxychromenone-derived esters/amides under mild conditions with good to excellent yields and broad substrate scope.
摘要
一种新型的 N-杂环卡宾促进的 3-羟基色烯酮的对映选择性 C2-官能化的合成方法，建立了α，β-不饱和酰基氮唑中间体的形成，该中间体通过 Coates-Claisen 重排发生。这种合成策略使在温和条件下以良好至优异的收率和广泛的底物范围快速组装对映体富集的δ-羟基色烯酮衍生的酯/酰胺成为可能。
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