Organocatalytic Enantioselective [3+2] Cycloaddition of Azomethine Ylides with 2,4‐Dienals: Construction of Remote Stereogenic Centers via 1,6‐Addition Reaction,Advanced Synthesis & Catalysis

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Organocatalytic Enantioselective [3+2] Cycloaddition of Azomethine Ylides with 2,4‐Dienals: Construction of Remote Stereogenic Centers via 1,6‐Addition Reaction
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-09-18 , DOI: 10.1002/adsc.202000813
Hui Jiang ₁ , Leijie Zhou ₁ , Biming Mao ₂ , Chunhao Yuan ₁ , Wei Wang ₁ , Yongjun Wu ₁ , Cheng Zhang ₁ , Hongchao GUO ₁

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A regio‐ and stereoselective [3+2] cycloaddition of phthalazinium dicyanomethanides with 2,4‐dienals was achieved with the use of a commercially available MacMillan's calalyst via LUMO‐lowering activation. The reaction proceeds through 1,6‐additon to linear 2,4‐dienals with remote control over stereochemistry, affording the cycloadducts having three stereogenic centers.

中文翻译：

带有2,4-二烯醛的甲亚胺叶立德的有机催化对映选择性[3 + 2]环加成反应：通过1,6-加成反应构建远程立体中心

使用市售的MacMillan催化剂通过降低LUMO的活化作用，可以实现邻苯二甲酸和立体选择性的[3 + 2]邻苯二甲腈二氰胺与2,4二环的加成反应。反应通过1,6-己二醛进行，直至线性2,4-二烯醛，并可通过立体化学进行远程控制，从而得到具有三个立体异构中心的环加合物。

更新日期：2020-09-18

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