Chiral Bis-Oxalamide-Rare Earth Complex Catalyzed Inverse- Electron-Demand Asymmetric oxa-Hetero-Diels-Alder Reaction for Optically Active Dihydropyran Core Structures,Advanced Synthesis & Catalysis

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Chiral Bis-Oxalamide-Rare Earth Complex Catalyzed Inverse- Electron-Demand Asymmetric oxa-Hetero-Diels-Alder Reaction for Optically Active Dihydropyran Core Structures
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-11-19 , DOI: 10.1002/adsc.202200875
haodi yang ₁ , Jun-Bo Chen ₁ , Cheng Peng ₂ , Wen-Kai Liu ₂ , Sheng-Suo Zhou ₂ , Jiaxin Song ₃ , Zheng-Hang Qi ₂ , Yong Wang ₁ , Xing-Wang Wang ₂

Affiliation

Chiral bis-oxalamide (CBOA)/rare-earth metal complexes-catalyzed asymmetric inverse-electron-demand oxa-hetero-Diels-Alder (HDA) reactions were investigated under mild reaction conditions, which was performed between β,γ-unsaturated α-ketoesters and various electron-riched dienophiles, such as cyclopentadiene, 2,3-dihydrofuran, 3,4-dihydro-2H-pyran, tetrahydropyridine as well as phenyl(vinyl)sulfane. Several series of optically active functionalized 3,4-dihydro-2H-pyran or ring fused dihydropyran derivatives were obtained in high yields with high diastereo- and enantioselectivity. The procedure was able to tolerate a relatively wide range of substrates. The coordination mode of chiral bis-oxalamide with Sc(III) was demonstrated by the X-ray crystallographic structure, and DFT calculations were carried out to uncover the regio- and stereocontrol.

中文翻译：

手性双-草酰胺-稀土配合物催化的反电子需求不对称氧杂-杂-狄尔斯-桤木反应光学活性二氢吡喃核心结构

在温和的反应条件下，研究了手性双草酰胺（CBOA）/稀土金属配合物催化的不对称逆电子需求氧杂-杂-狄尔斯-阿尔德（HDA）反应，该反应在β，γ-不饱和α-之间进行酮酯和各种富电子亲二烯体，如环戊二烯、2,3-二氢呋喃、3,4-二氢-2H-吡喃、四氢吡啶以及苯基（乙烯基）硫烷。几个系列的旋光功能化3,4-二氢-2 H-吡喃或环稠合二氢吡喃衍生物以高产率和高非对映和对映选择性获得。该程序能够耐受相对广泛的底物。通过 X 射线晶体结构证明了手性双草酰胺与 Sc(III) 的配位模式，并进行了 DFT 计算以揭示区域和立体控制。

更新日期：2022-11-19

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