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

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

doi:10.1002/cjoc.202400764

Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (24) : 3393 -3398. DOI: 10.1002/cjoc.202400764

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

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Abstract

Comprehensive Summary: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.

Keywords

Pd-catalyzed / Asymmetric [4+4] cycloaddition / Indole-2, 3-quinodimethanes / 2-Alkylidenetrimethylene carbonates / Indole-fused eight-membered oxa-rings

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Xinhao Lu, Yi Wang, Chenghan He, Yang-Zi Liu, Wei-Ping Deng. Synthesis of Indole-Fused Eight-Membered Oxa-Rings via Palladium-Catalyzed Asymmetric [4+4] Cycloaddition of Indole-2, 3-Quinodimethanes with 2-Alkylidenetrimethylene Carbonates. Chinese Journal of Chemistry, 2024, 42(24): 3393-3398 DOI:10.1002/cjoc.202400764