Asymmetric Synthesis of Dihydrocoumarins via Squaramide-Catalyzed [4 + 2] Annulation Reaction of 2-Hydroxy α-Amido Sulfones and Azlactones.

IF 3.3 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal Pub Date : 2025-09-25 DOI:10.1002/asia.70334

Bin Pan, Fei-Xiang He, Qiu-Yu Liao, Ming Liu, Lei Zhu, Sheng-Li Niu, Wu Liang, Fei Du, Ting Liu, Qin Ouyang

引用次数: 0

Abstract

An efficient asymmetric organocatalytic [4 + 2] annulation of 2-hydroxy α-amido sulfones with azlactones in the present of a chiral squaramide has been successfully developed. This protocol furnishes a series of enantioenriched multi-substituted dihydrocoumarin derivatives with high yields (up to 96%), good to excellent stereoselectivities (up to >20:1 dr, 82%-99% ee) under mild reaction conditions. The method has demonstrated a rapid preparation of highly functionalized dihydrocoumarins, which will enrich the field of the catalytic asymmetric reactions of azlactones. Moreover, the large-scale reaction, straightforward derivatization of chiral products highlight the practical value of this method.

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squar酰胺催化2-羟基α-氨基砜与氮唑内酯[4 + 2]环化反应合成二氢香豆素。

在手性方酰胺的存在下，成功地建立了2-羟基α-氨基砜与氮内酯的高效不对称有机催化[4 + 2]环化反应。该方案提供了一系列对映体富集的多取代双氢香豆素衍生物，在温和的反应条件下，具有高收率（高达96%），良好至优异的立体选择性（高达>20:1 dr, 82%-99% ee）。该方法可快速制备高功能化的二氢香豆素，丰富了氮唑内酯催化不对称反应的研究领域。此外，该方法反应规模大，手性产物衍生化简单，突出了该方法的实用价值。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Chemistry - An Asian Journal 化学-化学综合

CiteScore

7.00

自引率

2.40%

发文量

535

审稿时长

1.3 months

期刊介绍： Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics. Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews. A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal. Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).