螺旋手性阴离子对映选择性pictet - spengler型反应制备4,5-二氢吡咯[1,2-a]喹啉支架。

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-07-01 DOI:10.1021/acs.joc.5c00638

Martin Nigríni,Filip Uhlík,Ivana Císařová,Jan Veselý

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引用次数: 0

摘要

我们报道了一种对映选择性pictet - spengler型反应，该反应是由一种成本低廉且易于获得的螺旋手性环戊二烯（PCCP）催化剂实现的。该方法在温和的反应条件下进行，有利于合成一类新的手性4,5-二氢吡咯[1,2-a]喹诺啉（DHPQs），其特点是由于分子内氢键而增强了抗芳构化的能力。此外，该协议具有广泛的衬底兼容性，并展示了显著的合成多功能性。

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

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-a]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.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.