Decarboxylative Intramolecular Cyclization and Sequential Halogenation of Cyclic Enol Carbonates ®Synthesis of Stereochemically-defined Seven-membered Carbocycles®

Haruki Yokoyama; Natsuki Kimaru; Akane Kozuma; Keiichi Komatsuki; Tohru Yamada; Kodai Saito

doi:10.1246/cl.220211

Decarboxylative Intramolecular Cyclization and Sequential Halogenation of Cyclic Enol Carbonates ®Synthesis of Stereochemically-defined Seven-membered Carbocycles®

Haruki Yokoyama, Natsuki Kimaru, Akane Kozuma, Keiichi Komatsuki, Tohru Yamada, Kodai Saito

Department of Chemistry

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

3 Citations (Scopus)

Abstract

The intramolecular cyclization for the construction of 7-membered carbocycles triggered by the decarboxylation of a cyclic enol carbonate was studied. In this study, it was found that the treatment of the alkene-tethered cyclic enol carbonate with a metal halide resulted in the decarboxylation and sequential intramolecular cyclization, followed by halogenation to give a functionalized 7-membered ketone with high stereoselectivity. Among the Lewis acidic metal halides, titanium tetrachloride was the most effective for this transformation. This method was applicable for a variety of substrates.

Original language	English
Pages (from-to)	867-869
Number of pages	3
Journal	Chemistry Letters
Volume	51
Issue number	8
DOIs	https://doi.org/10.1246/cl.220211
Publication status	Published - 2022 Aug

Keywords

Cyclization
Decarboxylation
Seven-membered ring

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.220211

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title = "Decarboxylative Intramolecular Cyclization and Sequential Halogenation of Cyclic Enol Carbonates {\textregistered}Synthesis of Stereochemically-defined Seven-membered Carbocycles{\textregistered}",

abstract = "The intramolecular cyclization for the construction of 7-membered carbocycles triggered by the decarboxylation of a cyclic enol carbonate was studied. In this study, it was found that the treatment of the alkene-tethered cyclic enol carbonate with a metal halide resulted in the decarboxylation and sequential intramolecular cyclization, followed by halogenation to give a functionalized 7-membered ketone with high stereoselectivity. Among the Lewis acidic metal halides, titanium tetrachloride was the most effective for this transformation. This method was applicable for a variety of substrates.",

keywords = "Cyclization, Decarboxylation, Seven-membered ring",

author = "Haruki Yokoyama and Natsuki Kimaru and Akane Kozuma and Keiichi Komatsuki and Tohru Yamada and Kodai Saito",

note = "Publisher Copyright: {\textcopyright} 2022 The Chemical Society of Japan.",

year = "2022",

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language = "English",

volume = "51",

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T1 - Decarboxylative Intramolecular Cyclization and Sequential Halogenation of Cyclic Enol Carbonates ®Synthesis of Stereochemically-defined Seven-membered Carbocycles®

AU - Yokoyama, Haruki

AU - Kimaru, Natsuki

AU - Kozuma, Akane

AU - Komatsuki, Keiichi

AU - Yamada, Tohru

AU - Saito, Kodai

PY - 2022/8

Y1 - 2022/8

N2 - The intramolecular cyclization for the construction of 7-membered carbocycles triggered by the decarboxylation of a cyclic enol carbonate was studied. In this study, it was found that the treatment of the alkene-tethered cyclic enol carbonate with a metal halide resulted in the decarboxylation and sequential intramolecular cyclization, followed by halogenation to give a functionalized 7-membered ketone with high stereoselectivity. Among the Lewis acidic metal halides, titanium tetrachloride was the most effective for this transformation. This method was applicable for a variety of substrates.

AB - The intramolecular cyclization for the construction of 7-membered carbocycles triggered by the decarboxylation of a cyclic enol carbonate was studied. In this study, it was found that the treatment of the alkene-tethered cyclic enol carbonate with a metal halide resulted in the decarboxylation and sequential intramolecular cyclization, followed by halogenation to give a functionalized 7-membered ketone with high stereoselectivity. Among the Lewis acidic metal halides, titanium tetrachloride was the most effective for this transformation. This method was applicable for a variety of substrates.

KW - Cyclization

KW - Decarboxylation

KW - Seven-membered ring

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Decarboxylative Intramolecular Cyclization and Sequential Halogenation of Cyclic Enol Carbonates ®Synthesis of Stereochemically-defined Seven-membered Carbocycles®

Abstract

Keywords

ASJC Scopus subject areas

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