Direct C4-Benzylation of Indoles via Tandem Benzyl Claisen/Cope Rearrangements

Takumi Abe; Yuta Kosaka; Miku Asano; Natsuki Harasawa; Akane Mishina; Misato Nagasue; Yuri Sugimoto; Kazuaki Katakawa; Shunsuke Sueki; Masahiro Anada; Koji Yamada

doi:10.1021/acs.orglett.8b04120

Direct C4-Benzylation of Indoles via Tandem Benzyl Claisen/Cope Rearrangements

Takumi Abe, Yuta Kosaka, Miku Asano, Natsuki Harasawa, Akane Mishina, Misato Nagasue, Yuri Sugimoto, Kazuaki Katakawa, Shunsuke Sueki, Masahiro Anada, Koji Yamada

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

14 Citations (Scopus)

Abstract

A novel direct C4 benzylation of indoles utilizing 2-benzyloxyindoles has been developed to access 4-benzyl-2-oxindoles. This strategy involves the in situ formation of isotoluene intermediates via benzyl Claisen rearrangements, which undergoes Cope rearrangement and aromatization. The method provides the desired products in moderate to high yields and shows good functional group tolerance.

Original language	English
Pages (from-to)	826-829
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	3
DOIs	https://doi.org/10.1021/acs.orglett.8b04120
Publication status	Published - Feb 1 2019
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b04120

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title = "Direct C4-Benzylation of Indoles via Tandem Benzyl Claisen/Cope Rearrangements",

abstract = "A novel direct C4 benzylation of indoles utilizing 2-benzyloxyindoles has been developed to access 4-benzyl-2-oxindoles. This strategy involves the in situ formation of isotoluene intermediates via benzyl Claisen rearrangements, which undergoes Cope rearrangement and aromatization. The method provides the desired products in moderate to high yields and shows good functional group tolerance.",

author = "Takumi Abe and Yuta Kosaka and Miku Asano and Natsuki Harasawa and Akane Mishina and Misato Nagasue and Yuri Sugimoto and Kazuaki Katakawa and Shunsuke Sueki and Masahiro Anada and Koji Yamada",

note = "Funding Information: This work was financially supported by JSPS KAKENHI Grant No. 16K18849 (T.A.) Grant-in-Aid for Young Scientists (B). Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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doi = "10.1021/acs.orglett.8b04120",

language = "English",

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T1 - Direct C4-Benzylation of Indoles via Tandem Benzyl Claisen/Cope Rearrangements

AU - Abe, Takumi

AU - Kosaka, Yuta

AU - Asano, Miku

AU - Harasawa, Natsuki

AU - Mishina, Akane

AU - Nagasue, Misato

AU - Sugimoto, Yuri

AU - Katakawa, Kazuaki

AU - Sueki, Shunsuke

AU - Anada, Masahiro

AU - Yamada, Koji

PY - 2019/2/1

Y1 - 2019/2/1

N2 - A novel direct C4 benzylation of indoles utilizing 2-benzyloxyindoles has been developed to access 4-benzyl-2-oxindoles. This strategy involves the in situ formation of isotoluene intermediates via benzyl Claisen rearrangements, which undergoes Cope rearrangement and aromatization. The method provides the desired products in moderate to high yields and shows good functional group tolerance.

AB - A novel direct C4 benzylation of indoles utilizing 2-benzyloxyindoles has been developed to access 4-benzyl-2-oxindoles. This strategy involves the in situ formation of isotoluene intermediates via benzyl Claisen rearrangements, which undergoes Cope rearrangement and aromatization. The method provides the desired products in moderate to high yields and shows good functional group tolerance.

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JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Direct C4-Benzylation of Indoles via Tandem Benzyl Claisen/Cope Rearrangements

Abstract

ASJC Scopus subject areas

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