Synthesis of Indole-Fused Eight-Membered Oxa-Rings via Palladium-Catalyzed Asymmetric [4+4] Cycloaddition of Indole-2,3-Quinodimethanes with 2-Alkylidenetrimethylene Carbonates

IF 5.5 1区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chinese Journal of Chemistry Pub Date : 2024-09-16 DOI:10.1002/cjoc.202400764

Xinhao Lu, Yi Wang, Chenghan He, Yang-Zi Liu, Wei-Ping Deng

引用次数: 0

Abstract

We report a palladium-catalyzed asymmetric [4+4] cycloaddition reaction between 2-alkylidenetrimethylene carbonate and electron-deficient indole-2,3-quinodimethanes (IQDMs). This reaction features exclusive regioselectivity, high yield (up to 98%), excellent enantioselectivity (up to 95% ee), and easy scale-up without any loss of efficiency, making it valuable for the synthesis of indole-fused eight-membered oxa-rings.

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钯催化吲哚-2,3-喹二甲烷与 2-亚烷基三亚甲基碳酸酯的不对称 [4+4] 环加成法合成吲哚融合的八分子 Oxa-Rings

我们报告了在钯催化下，2-亚烷基三亚甲基碳酸酯与缺电子的吲哚-2,3-醌二甲烷（IQDMs）之间的不对称[4+4]环加成反应。该反应具有独特的区域选择性、高产率（高达 98%）、优异的对映选择性（高达 95% ee），并且易于放大而不会降低效率，因此在合成吲哚融合的八元氧环方面具有重要价值。

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

Chinese Journal of Chemistry 化学-化学综合

CiteScore

8.80

自引率

14.80%

发文量

422

审稿时长

1.7 months

期刊介绍： The Chinese Journal of Chemistry is an international forum for peer-reviewed original research results in all fields of chemistry. Founded in 1983 under the name Acta Chimica Sinica English Edition and renamed in 1990 as Chinese Journal of Chemistry, the journal publishes a stimulating mixture of Accounts, Full Papers, Notes and Communications in English.