Stereocontrolled Construction of Spirooxindole-Containing 5,6,7,8-Tetrahydropyrrolo[1,2-a]pyridine via Michael/Friedel–Crafts Domino Reaction Promoted by Secondary Amine-Squaramide,Organic Letters

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Stereocontrolled Construction of Spirooxindole-Containing 5,6,7,8-Tetrahydropyrrolo[1,2-a]pyridine via Michael/Friedel–Crafts Domino Reaction Promoted by Secondary Amine-Squaramide
Organic Letters ( IF 4.9 ) Pub Date : 2024-03-08 , DOI: 10.1021/acs.orglett.4c00073
Pengxuan Yin ₁ , Zijie Zhou ₁ , Lingsheng Shi ₁ , Chengzhi Xiang ₁ , Ling Ye ₂ , Min Han ₁ , Zhichuan Shi ₁ , Zhigang Zhao ₁ , Xuefeng Li ₁

Affiliation

An asymmetric Michael/Friedel–Crafts cascade reaction with Morita–Baylis–Hillman (MBH) nitroallylic esters and 3-pyrrolyloxindoles has been developed for the stereoselective construction of spirooxindole-containing tetrahydroindolizines. A range of tetracyclic scaffolds possessing three consecutive chiral centers, including an all-carbon quaternary stereocenter, were generated in 53–85% isolated yields with high diastereoselectivities and enantiopurities (≥3:1 dr, 50–98% ee). A newly synthesized bifunctional secondary amine/squaramide organocatalyst was demonstrated to exhibit better stereochemical control than their tertiary analogues.

中文翻译：

仲胺-方酰胺促进的 Michael/Friedel-Crafts 多米诺反应立体控制构建含螺吲哚的 5,6,7,8-四氢吡咯并[1,2-a]吡啶

已开发出一种使用 Morita-Baylis-Hillman (MBH) 硝基烯丙酯和 3-吡咯吲哚的不对称 Michael/Friedel-Crafts 级联反应，用于立体选择性构建含螺吲哚的四氢吲嗪。一系列具有三个连续手性中心（包括全碳四元立构中心）的四环支架以 53-85% 的分离产率生成，具有高非对映选择性和对映体纯度（≥3:1 dr，50-98% ee）。新合成的双功能仲胺/方酰胺有机催化剂被证明比其三级类似物表现出更好的立体化学控制。

更新日期：2024-03-08

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