Stereoselective formal alkenylation of β,β-disubstituted enesulfinamides for constructing 1,5- and 1,4-dicarbonyl derivatives bearing less-accessible acyclic α-quaternary stereocenters,Organic Chemistry Frontiers

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Stereoselective formal alkenylation of β,β-disubstituted enesulfinamides for constructing 1,5- and 1,4-dicarbonyl derivatives bearing less-accessible acyclic α-quaternary stereocenters
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2023-09-28 , DOI: 10.1039/d3qo01381b
Chong-Lin Zhu _{1,

2} , Chong-Dao Lu _{1,

3}

Affiliation

Geometry-defined β,β-disubstituted enesulfinamides undergo one-pot conjugate addition–elimination cascade to afford α-alkenylated ketimines with high stereocontrol. By tuning the substituents on Michael acceptors, formal alkenylation transformation allows regiodivergent construction of 1,5- and 1,4-dicarbonyl derivatives bearing less-accessible acyclic quaternary α-stereocenters substituted with two sterically and electronically similar groups (e.g., methyl and ethyl).

中文翻译：

β,β-二取代烯亚磺酰胺的立体选择性形式烯基化，用于构建带有不易接近的无环 α-四元立构中心的 1,5- 和 1,4-二羰基衍生物

几何定义的 β,β-二取代烯亚磺酰胺经过一锅共轭加成-消除级联，得到具有高度立体控制的 α-烯基化酮亚胺。通过调整迈克尔受体上的取代基，正式的烯基化转化允许区域发散地构建带有不易接近的无环四元α-立构中心的1,5-和1,4-二羰基衍生物，并被两个空间和电子相似的基团（例如甲基和乙基）取代。

更新日期：2023-09-28

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