Synthesis of β-lactams via diastereoselective, intramolecular Kinugasa reactions.,Organic & Biomolecular Chemistry

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Synthesis of β-lactams via diastereoselective, intramolecular Kinugasa reactions.
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-04-15 , DOI: 10.1039/d0ob00228c
Oskar Popik ₁ , Barbara Grzeszczyk ₁ , Olga Staszewska-Krajewska ₁ , Bartłomiej Furman ₁ , Marek Chmielewski ₁

Affiliation

Intramolecular Kinugasa reactions on in situ generated carbohydrate-derived alkynylnitrones are described. The effects of the length of chains, their mutual configuration, influence of experimental conditions on product distribution and feasibility of the β-lactam ring construction were studied. Intramolecular reactions proceed with high stereoselectivity to provide in each case one product only. The cycloadducts from tartaric acid were converted into the corresponding non-racemic 4-acetoxy azetidinones in good yields.

中文翻译：

通过非对映选择性分子内Kinugasa反应合成β-内酰胺。

描述了在原位产生的碳水化合物衍生的炔基硝基酮上的分子内Kinugasa反应。研究了链长，互构，实验条件对产物分布的影响以及构建β-内酰胺环的可行性。分子内反应以高立体选择性进行，在每种情况下仅提供一种产物。来自酒石酸的环加合物以良好的产率转化为相应的非外消旋的4-乙酰氧基氮杂环丁烷酮。

更新日期：2020-04-24

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