Lewis acid-catalyzed double addition of indoles to ketones: Synthesis of bis(indolyl)methanes with all-carbon quaternary centers

Si On Lee; Jeongin Choi; Seunghoon Kook; Sarah Yunmi Lee

doi:10.1039/d0ob01916j

Lewis acid-catalyzed double addition of indoles to ketones: Synthesis of bis(indolyl)methanes with all-carbon quaternary centers

Si On Lee, Jeongin Choi, Seunghoon Kook, Sarah Yunmi Lee

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

We report herein a Lewis acid-catalyzed nucleophilic double-addition of indoles to ketones under mild conditions. This process occurs with various ketones ranging from dialkyl ketones to diaryl ketones, thereby providing access to an array of bis(indolyl)methanes bearing all-carbon quaternary centers, including tetra-aryl carbon centers. The products can be transformed into bis(indole)-fused polycyclics and bis(indolyl)alkenes.

Original language	English
Pages (from-to)	9060-9064
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	18
Issue number	44
DOIs	https://doi.org/10.1039/d0ob01916j
Publication status	Published - 2020 Nov 28

Bibliographical note

Funding Information:
This work was supported by (1) the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT & Future Planning (2018R1C1B6005712), (2) the Yonsei University Future-leading Research Initiative of 2018 (22-0055), and (3) the POSCO Cheongam Foundation (fellowship to S. Y. L.).

Publisher Copyright:
© The Royal Society of Chemistry.

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/d0ob01916j

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title = "Lewis acid-catalyzed double addition of indoles to ketones: Synthesis of bis(indolyl)methanes with all-carbon quaternary centers",

abstract = "We report herein a Lewis acid-catalyzed nucleophilic double-addition of indoles to ketones under mild conditions. This process occurs with various ketones ranging from dialkyl ketones to diaryl ketones, thereby providing access to an array of bis(indolyl)methanes bearing all-carbon quaternary centers, including tetra-aryl carbon centers. The products can be transformed into bis(indole)-fused polycyclics and bis(indolyl)alkenes.",

author = "Lee, {Si On} and Jeongin Choi and Seunghoon Kook and Lee, {Sarah Yunmi}",

note = "Funding Information: This work was supported by (1) the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT & Future Planning (2018R1C1B6005712), (2) the Yonsei University Future-leading Research Initiative of 2018 (22-0055), and (3) the POSCO Cheongam Foundation (fellowship to S. Y. L.). Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

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AU - Choi, Jeongin

AU - Kook, Seunghoon

AU - Lee, Sarah Yunmi

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PY - 2020/11/28

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N2 - We report herein a Lewis acid-catalyzed nucleophilic double-addition of indoles to ketones under mild conditions. This process occurs with various ketones ranging from dialkyl ketones to diaryl ketones, thereby providing access to an array of bis(indolyl)methanes bearing all-carbon quaternary centers, including tetra-aryl carbon centers. The products can be transformed into bis(indole)-fused polycyclics and bis(indolyl)alkenes.

AB - We report herein a Lewis acid-catalyzed nucleophilic double-addition of indoles to ketones under mild conditions. This process occurs with various ketones ranging from dialkyl ketones to diaryl ketones, thereby providing access to an array of bis(indolyl)methanes bearing all-carbon quaternary centers, including tetra-aryl carbon centers. The products can be transformed into bis(indole)-fused polycyclics and bis(indolyl)alkenes.

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Lewis acid-catalyzed double addition of indoles to ketones: Synthesis of bis(indolyl)methanes with all-carbon quaternary centers

Abstract

Bibliographical note

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