Synthesis of Oxygen-Containing Heterocyclic Compounds by Iron-Catalyzed Alkylative Cyclization of Unsaturated Carboxylic Acids and Alcohols

Masayuki Iwasaki; Yasuki Kazao; Takumi Ishida; Yasushi Nishihara

doi:10.1021/acs.orglett.0c02671

Synthesis of Oxygen-Containing Heterocyclic Compounds by Iron-Catalyzed Alkylative Cyclization of Unsaturated Carboxylic Acids and Alcohols

Masayuki Iwasaki, Yasuki Kazao, Takumi Ishida, Yasushi Nishihara

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

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Abstract

Iron-catalyzed alkylative cyclization of alkenes bearing oxygen nucleophiles with secondary and tertiary alkyl bromides through carbon-carbon and carbon-oxygen bond formations has been developed. A broad substrate scope is an attractive feature of this synthetic method, providing a variety of potentially bioactive five- A nd six-membered oxygen-containing heterocycles. The reaction pathway is proposed to involve a radical addition of the in situ-formed alkyl radical to an alkene followed by carbon-oxygen bond-forming intramolecular cyclization.

Original language	English
Pages (from-to)	7343-7347
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	18
DOIs	https://doi.org/10.1021/acs.orglett.0c02671
Publication status	Published - Sep 18 2020

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthesis of Oxygen-Containing Heterocyclic Compounds by Iron-Catalyzed Alkylative Cyclization of Unsaturated Carboxylic Acids and Alcohols",

abstract = "Iron-catalyzed alkylative cyclization of alkenes bearing oxygen nucleophiles with secondary and tertiary alkyl bromides through carbon-carbon and carbon-oxygen bond formations has been developed. A broad substrate scope is an attractive feature of this synthetic method, providing a variety of potentially bioactive five- A nd six-membered oxygen-containing heterocycles. The reaction pathway is proposed to involve a radical addition of the in situ-formed alkyl radical to an alkene followed by carbon-oxygen bond-forming intramolecular cyclization. ",

author = "Masayuki Iwasaki and Yasuki Kazao and Takumi Ishida and Yasushi Nishihara",

note = "Funding Information: This work was partly supported by a Grant-in-Aid for Scientific Research (KAKENHI) (16K17901) from JSPS. The authors gratefully thank Megumi Kosaka and Motonari Kobayashi (Department of Instrumental Analysis, Advanced Science Research Center, Okayama University) for performing elemental analyses and the SC-NMR Laboratory (Okayama University) for the NMR spectral measurements. Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

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doi = "10.1021/acs.orglett.0c02671",

language = "English",

volume = "22",

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journal = "Organic Letters",

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AU - Iwasaki, Masayuki

AU - Kazao, Yasuki

AU - Ishida, Takumi

AU - Nishihara, Yasushi

N1 - Funding Information: This work was partly supported by a Grant-in-Aid for Scientific Research (KAKENHI) (16K17901) from JSPS. The authors gratefully thank Megumi Kosaka and Motonari Kobayashi (Department of Instrumental Analysis, Advanced Science Research Center, Okayama University) for performing elemental analyses and the SC-NMR Laboratory (Okayama University) for the NMR spectral measurements. Publisher Copyright: © 2020 American Chemical Society.

PY - 2020/9/18

Y1 - 2020/9/18

N2 - Iron-catalyzed alkylative cyclization of alkenes bearing oxygen nucleophiles with secondary and tertiary alkyl bromides through carbon-carbon and carbon-oxygen bond formations has been developed. A broad substrate scope is an attractive feature of this synthetic method, providing a variety of potentially bioactive five- A nd six-membered oxygen-containing heterocycles. The reaction pathway is proposed to involve a radical addition of the in situ-formed alkyl radical to an alkene followed by carbon-oxygen bond-forming intramolecular cyclization.

AB - Iron-catalyzed alkylative cyclization of alkenes bearing oxygen nucleophiles with secondary and tertiary alkyl bromides through carbon-carbon and carbon-oxygen bond formations has been developed. A broad substrate scope is an attractive feature of this synthetic method, providing a variety of potentially bioactive five- A nd six-membered oxygen-containing heterocycles. The reaction pathway is proposed to involve a radical addition of the in situ-formed alkyl radical to an alkene followed by carbon-oxygen bond-forming intramolecular cyclization.

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Synthesis of Oxygen-Containing Heterocyclic Compounds by Iron-Catalyzed Alkylative Cyclization of Unsaturated Carboxylic Acids and Alcohols

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