Enantioselective sequential Michael addition/C-H olefination/Michael reaction for the efficient collective synthesis of clavine alkaloids

IF 7.9 2区 综合性期刊 Q1 CHEMISTRY, MULTIDISCIPLINARY Cell Reports Physical Science Pub Date : 2024-07-22 DOI:10.1016/j.xcrp.2024.102112
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Abstract

Sequential reactions are important for the direct and convenient synthesis of complex molecules with multiple chiral centers. Here, we report an enantioselective sequential Michael addition/C–H olefination/Michael addition reaction for the asymmetric construction of chiral 2-aminotetralin derivatives bearing three stereogenic centers using readily accessible 2-aryl N-quinolyl acrylamide, nitromethane, and alkenyl iodide. This optimized process utilizes a quinine-based squaramide bifunctional organocatalyst in the enantioselective Michael addition of nitromethane to a conjugated amide. Subsequently, the N,N-bidentate amide-directed Pd-catalyzed C–H olefination of the 2-arylamide and intramolecular Michael addition of a conjugated ester generates tetralins with high enantioselectivities and good stereoselectivities and yields. To demonstrate the synthetic utility of this sequential reaction, the collective synthesis of various clavine alkaloids with different skeletons is accomplished from a common tricyclic intermediate that can be readily prepared using chiral 2-aminotetralins.

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对映体选择性顺序迈克尔加成/C-H 烯化/迈克尔反应用于高效集体合成黄烷生物碱
顺序反应对于直接方便地合成具有多个手性中心的复杂分子非常重要。在此,我们报告了一种对映选择性迈克尔加成/C-H 烯化/迈克尔加成顺序反应,利用容易获得的 2-芳基 N-喹啉丙烯酰胺、硝基甲烷和烯基碘化物,不对称地构建具有三个立体中心的手性 2-氨基四氢萘衍生物。该优化工艺利用一种基于奎宁的方酰胺双功能有机催化剂,将硝基甲烷与共轭酰胺进行对映选择性迈克尔加成反应。随后,N,N-二叉酰胺定向钯催化 2-芳酰胺的 C-H 烯化反应和共轭酯的分子内迈克尔加成反应生成对映选择性高、立体选择性好且产率高的四氢萘。为了证明这种连续反应的合成效用,我们从一种常见的三环中间体出发,完成了具有不同骨架的各种黄烷生物碱的集体合成,这种三环中间体可以使用手性 2-氨基四氢萘轻松制备。
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来源期刊
Cell Reports Physical Science
Cell Reports Physical Science Energy-Energy (all)
CiteScore
11.40
自引率
2.20%
发文量
388
审稿时长
62 days
期刊介绍: Cell Reports Physical Science, a premium open-access journal from Cell Press, features high-quality, cutting-edge research spanning the physical sciences. It serves as an open forum fostering collaboration among physical scientists while championing open science principles. Published works must signify significant advancements in fundamental insight or technological applications within fields such as chemistry, physics, materials science, energy science, engineering, and related interdisciplinary studies. In addition to longer articles, the journal considers impactful short-form reports and short reviews covering recent literature in emerging fields. Continually adapting to the evolving open science landscape, the journal reviews its policies to align with community consensus and best practices.
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