Asymmetric synthesis of cyclopenta[<i>b</i>]indoles <i>via</i> organocatalytic formal (3 + 2) cyclization of β-keto ester with azonaphthalene

Song, Yanji; Shi, Ting; Chen, Qianping; Tan, Qingfa; Cao, Weidi; Feng, Xiaoming; Liu, Xiaohua

doi:10.1039/d3qo00306j

Org. Chem. Front.

2023

DOI: 10.1039/d3qo00306j

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Asymmetric synthesis of cyclopenta[b]indoles via organocatalytic formal (3 + 2) cyclization of β-keto ester with azonaphthalene

Yanji Song

Ting Shi

Qianping Chen

et al.

Abstract: Enatioselective formal [3+2] cyclization of cyclic β-keto esters with azonaphthalenes has been established. A range of cyclopenta[b]indoles have been synthesized in good yield (up to 99% yield) with high diastereo-...

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Cited by 3 publications

References 63 publications

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Regioselective Construction of Indolylated Cyclic Tetrasubstituted Carbon Centers through Brønsted Acid‐Catalyzed Dearomative Skeletal Rearrangement of Azofurans

Zhang,

Bao,

et al. 2023

Adv Synth Catal

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A Brønsted acid‐catalyzed dearomative skeletal rearrangement of azofurans with indoles is reported, enabling a regioselective 1,6‐addition, ring‐opening and 1,4‐addition cascade to produce 26 examples of indolylated pyrrol‐2‐ones with a cyclic tetrasubstituted stereocenter in 58–94% yields. This protocol demonstrates remarkable compatibility regarding azofurans and indoles with different substitution patterns, featuring complete regioselectivity.

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Regioselective Construction of Indolylated Cyclic Tetrasubstituted Carbon Centers through Brønsted Acid‐Catalyzed Dearomative Skeletal Rearrangement of Azofurans

Zhang,

Bao,

et al. 2023

Adv Synth Catal

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Asymmetric Synthesis of Hydroindoles via Desymmetrizing [3+2] Annulation of p-Quinamines and Arylalkylketenes

Chen,

Zhang,

Song

et al. 2024

Org. Lett.

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The asymmetric desymmetrizing [3+2] annulation reaction of p-quinamines and arylalkylketenes to synthesize hydroindoles was realized. Catalyzed by chiral bisguanidinium hemisalt via multiple hydrogen bond interactions, enantiomerically enriched products with reversal of diastereoselectivity in comparison with the racemic version were afforded in good yields under mild reaction conditions. Diaryl-substituted hydroindoles could also perform the Friedel−Crafts type of addition to give more complicated multicycles. Density functional theory calculations revealed that the enantio-and diastereoselectivity stem from varied hydrogen-bonding manners.

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Ir/Brønsted acid dual-catalyzed asymmetric synthesis of bisbenzannulated spiroketals and spiroaminals from isochroman ketals

Chen,

Yan,

Zheng

et al. 2024

Org. Chem. Front.

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Asymmetric synthesis of cyclopenta[b]indoles via organocatalytic formal (3 + 2) cyclization of β-keto ester with azonaphthalene

Abstract: Enatioselective formal [3+2] cyclization of cyclic β-keto esters with azonaphthalenes has been established. A range of cyclopenta[b]indoles have been synthesized in good yield (up to 99% yield) with high diastereo-...

Cited by 3 publications

References 63 publications

Regioselective Construction of Indolylated Cyclic Tetrasubstituted Carbon Centers through Brønsted Acid‐Catalyzed Dearomative Skeletal Rearrangement of Azofurans

Regioselective Construction of Indolylated Cyclic Tetrasubstituted Carbon Centers through Brønsted Acid‐Catalyzed Dearomative Skeletal Rearrangement of Azofurans

Asymmetric Synthesis of Hydroindoles via Desymmetrizing [3+2] Annulation of p-Quinamines and Arylalkylketenes

Ir/Brønsted acid dual-catalyzed asymmetric synthesis of bisbenzannulated spiroketals and spiroaminals from isochroman ketals

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