Indole Editing Enabled by HFIP-Mediated Ring-Switch Reactions of 3-Amino-2-Hydroxyindolines

Takumi Abe; Toshiki Yamashiro; Kaho Shimizu; Daisuke Sawada

doi:10.1002/chem.202201113

Indole Editing Enabled by HFIP-Mediated Ring-Switch Reactions of 3-Amino-2-Hydroxyindolines

Takumi Abe, Toshiki Yamashiro, Kaho Shimizu, Daisuke Sawada

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

3 Citations (Scopus)

Abstract

This work reports the novel reactivity of hemiaminal as a precursor for indole editing at the multi-site. The HFIP-promoted indole editing of indoline hemiaminals affords 2-arylindoles through a ring-switch sequence. The key to success of this transformation is to use a cyclic hemiaminal as an α-amino aldehyde surrogate under transient tautomeric control. This transformation features mild reaction conditions and good yields with broad functional group tolerance. The utility of this transformation is presented through the one-pot protocol and the synthesis of isocryptolepine.

Original language	English
Journal	Chemistry - A European Journal
DOIs	https://doi.org/10.1002/chem.202201113
Publication status	Accepted/In press - 2022

Keywords

hemiaminals
HFIP
indoles
molecule editing
ring-switch

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.202201113

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title = "Indole Editing Enabled by HFIP-Mediated Ring-Switch Reactions of 3-Amino-2-Hydroxyindolines",

abstract = "This work reports the novel reactivity of hemiaminal as a precursor for indole editing at the multi-site. The HFIP-promoted indole editing of indoline hemiaminals affords 2-arylindoles through a ring-switch sequence. The key to success of this transformation is to use a cyclic hemiaminal as an α-amino aldehyde surrogate under transient tautomeric control. This transformation features mild reaction conditions and good yields with broad functional group tolerance. The utility of this transformation is presented through the one-pot protocol and the synthesis of isocryptolepine.",

keywords = "hemiaminals, HFIP, indoles, molecule editing, ring-switch",

author = "Takumi Abe and Toshiki Yamashiro and Kaho Shimizu and Daisuke Sawada",

note = "Funding Information: This work was partially supported by Grants‐in‐Aid for KAKENHI S (17H06173) from the Ministry of Education, Culture, Sports, Sciences and Technology (MEXT) of the Japan Society for the Promotion of Sciences (JSPS). We are very grateful to Dr. Masaru Tanioka and Prof. Shinichiro Kamino (School of Pharmaceutical Sciences, Aichi Gakuin University) for X‐ray diffraction analysis. T. Y. thanks Nagai Memorial Research Scholarship from the Pharmaceutical Society of Japan. Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

year = "2022",

doi = "10.1002/chem.202201113",

language = "English",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

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T1 - Indole Editing Enabled by HFIP-Mediated Ring-Switch Reactions of 3-Amino-2-Hydroxyindolines

AU - Abe, Takumi

AU - Yamashiro, Toshiki

AU - Shimizu, Kaho

AU - Sawada, Daisuke

N1 - Funding Information: This work was partially supported by Grants‐in‐Aid for KAKENHI S (17H06173) from the Ministry of Education, Culture, Sports, Sciences and Technology (MEXT) of the Japan Society for the Promotion of Sciences (JSPS). We are very grateful to Dr. Masaru Tanioka and Prof. Shinichiro Kamino (School of Pharmaceutical Sciences, Aichi Gakuin University) for X‐ray diffraction analysis. T. Y. thanks Nagai Memorial Research Scholarship from the Pharmaceutical Society of Japan. Publisher Copyright: © 2022 Wiley-VCH GmbH.

PY - 2022

Y1 - 2022

N2 - This work reports the novel reactivity of hemiaminal as a precursor for indole editing at the multi-site. The HFIP-promoted indole editing of indoline hemiaminals affords 2-arylindoles through a ring-switch sequence. The key to success of this transformation is to use a cyclic hemiaminal as an α-amino aldehyde surrogate under transient tautomeric control. This transformation features mild reaction conditions and good yields with broad functional group tolerance. The utility of this transformation is presented through the one-pot protocol and the synthesis of isocryptolepine.

AB - This work reports the novel reactivity of hemiaminal as a precursor for indole editing at the multi-site. The HFIP-promoted indole editing of indoline hemiaminals affords 2-arylindoles through a ring-switch sequence. The key to success of this transformation is to use a cyclic hemiaminal as an α-amino aldehyde surrogate under transient tautomeric control. This transformation features mild reaction conditions and good yields with broad functional group tolerance. The utility of this transformation is presented through the one-pot protocol and the synthesis of isocryptolepine.

KW - hemiaminals

KW - HFIP

KW - indoles

KW - molecule editing

KW - ring-switch

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DO - 10.1002/chem.202201113

M3 - Article

C2 - 35438809

AN - SCOPUS:85130376315

SN - 0947-6539

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

ER -

Indole Editing Enabled by HFIP-Mediated Ring-Switch Reactions of 3-Amino-2-Hydroxyindolines

Abstract

Keywords

ASJC Scopus subject areas

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