通过 4-溴吡唑酮和氮杂北喹酮甲苷的正式 [4+1] 嵌合反应，有机催化对映体选择性合成手性螺吲哚啉吡唑酮

IF 1.5 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Helvetica Chimica Acta Pub Date : 2024-03-06 DOI:10.1002/hlca.202400029

Laura Carceller-Ferrer, Carlos Rodríguez-Arias, Marc Montesinos-Magraner, Amparo Sanz-Marco, Judit Hostalet-Romero, Gonzalo Blay, José R. Pedro, Carlos Vila

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引用次数: 0

摘要

在这篇通讯中，介绍了一种直接不对称合成螺吲哚-吡唑酮化合物的方法。该方法包括在基本条件下，在 CHCl3 中由双喹啉衍生的方酰胺催化下，4-溴吡唑啉酮和原位生成的偶氮-正喹啉酮甲酯发生正式的 [4+1] 环加成反应。结果获得了多种含有吡唑酮和吲哚啉分子的手性螺环化合物，收率从中等到良好（高达 68%），对映选择性从中等到极佳（高达 93%ee）。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Organocatalytic Enantioselective Synthesis of Chiral Spiro-indoline-pyrazolones through a formal [4+1] Annulation Reaction of 4-Bromopyrazolones and aza-ortho-Quinone Methides

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Organocatalytic Enantioselective Synthesis of Chiral Spiro-indoline-pyrazolones through a formal [4+1] Annulation Reaction of 4-Bromopyrazolones and aza-ortho-Quinone Methides

In this communication, a straighforward asymmetric synthesis of spiro-indoline-pyrazolone compounds is described. This methodology consists in a formal [4+1] cycloaddition reaction of 4-bromopyrazolones and aza-ortho-quinone methides generated in situ catalyzed by a bisquinine-derived squaramide in CHCl₃ under basic conditions. A variety of chiral spirocyclic compounds bearing a pyrazolone and an indoline moieties were obtained in moderate to good yields (up to 68 %) and moderate to excellent enantioselectivities (up to 93 % ee).

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来源期刊

Helvetica Chimica Acta 化学-化学综合

CiteScore

3.00

自引率

0.00%

发文量

审稿时长

2.3 months

期刊介绍： Helvetica Chimica Acta, founded by the Swiss Chemical Society in 1917, is a monthly multidisciplinary journal dedicated to the dissemination of knowledge in all disciplines of chemistry (organic, inorganic, physical, technical, theoretical and analytical chemistry) as well as research at the interface with other sciences, where molecular aspects are key to the findings. Helvetica Chimica Acta is committed to the publication of original, high quality papers at the frontier of scientific research. All contributions will be peer reviewed with the highest possible standards and published within 3 months of receipt, with no restriction on the length of the papers and in full color.