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通过螺旋手性阴离子进行对映选择性 Pictet-Spengler 型反应以获得 4,5-二氢吡咯并[1,2-]喹喔啉骨架。

Enantioselective Pictet-Spengler-Type Reaction via a Helically Chiral Anion as an Access to 4,5-Dihydropyrrolo[1,2-]quinoxaline Scaffolds.

作者信息

Nigríni Martin, Uhlík Filip, Císařová Ivana, Veselý Jan

机构信息

Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 43 Prague, Czech Republic.

Department of Physical and Macromolecular Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 43 Prague, Czech Republic.

出版信息

J Org Chem. 2025 Jul 11;90(27):9380-9393. doi: 10.1021/acs.joc.5c00638. Epub 2025 Jul 1.

DOI:10.1021/acs.joc.5c00638
PMID:40590896
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12261325/
Abstract

We report an enantioselective Pictet-Spengler-type reaction enabled by a cost-effective and readily available helically chiral cyclopentadiene (PCCP) catalyst. This methodology, conducted under mild reaction conditions, facilitates the synthesis of a novel class of chiral 4,5-dihydropyrrolo[1,2-]quinoxalines (DHPQs) characterized by enhanced resistance to aromatization due to intramolecular hydrogen bonding. Additionally, the protocol exhibits broad substrate compatibility and demonstrates significant synthetic versatility.

摘要

我们报道了一种对映选择性Pictet-Spengler型反应，该反应由一种经济高效且易于获得的螺旋手性环戊二烯（PCCP）催化剂实现。这种方法在温和的反应条件下进行，有助于合成一类新型的手性4,5-二氢吡咯并[1,2-]喹喔啉（DHPQ），其特征在于由于分子内氢键作用而增强了对芳构化的抗性。此外，该方案具有广泛的底物兼容性，并展示出显著的合成多功能性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67c8/12261325/fe420d3851b1/jo5c00638_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67c8/12261325/44f3bc65eecc/jo5c00638_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67c8/12261325/fd980150940b/jo5c00638_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67c8/12261325/ca04ae4ca587/jo5c00638_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67c8/12261325/ccc0b33035c1/jo5c00638_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67c8/12261325/fe420d3851b1/jo5c00638_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67c8/12261325/44f3bc65eecc/jo5c00638_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67c8/12261325/fd980150940b/jo5c00638_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67c8/12261325/ca04ae4ca587/jo5c00638_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67c8/12261325/ccc0b33035c1/jo5c00638_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67c8/12261325/fe420d3851b1/jo5c00638_0005.jpg

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本文引用的文献

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Enantioenriched 1,4-Benzoxazepines via Chiral Brønsted Acid-Catalyzed Enantioselective Desymmetrization of 3-Substituted Oxetanes.通过手性布朗斯特酸催化3-取代氧杂环丁烷的对映选择性去对称化合成对映体富集的1,4-苯并二氮杂䓬类化合物
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