Synthesis of vinylidenecyclopropanes via gold(I)-catalyzed cyclopropanation of vinyl arenes with γ-stannylated propargyl esters

Hiroto Mori; Yusuke Ono; Shota Nakagawa; Sota Akima; Miki Murakami; Toshinobu Korenaga; Tadashi Nakaji-Hirabayashi; Mayumi Kyogoku; Yoshikazu Horino

doi:10.1039/D4CC04384G

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Synthesis of vinylidenecyclopropanes via gold(i)-catalyzed cyclopropanation of vinyl arenes with γ-stannylated propargyl esters†

Hiroto Mori,^a Yusuke Ono,^a Shota Nakagawa,^a Sota Akima,^a Miki Murakami,^b Toshinobu Korenaga,

*^cd Tadashi Nakaji-Hirabayashi,

^be Mayumi Kyogoku^b and Yoshikazu Horino

*^a

Author affiliations

* Corresponding authors

^a Department of Applied Chemistry and Bioscience, Chitose Institute of Science and Technology, Chitose, Japan
E-mail: y-horino@photon.chitose.ac.jp

^b Graduate School of Science and Engineering, University of Toyama, Toyama, Japan

^c Department of Applied Chemistry and Bioscience, Iwate University, Morioka, Japan
E-mail: korenaga@iwate-u.ac.jp

^d Soft-Path Science and Engineering Research Center (SPERC), Iwate University, Morioka, Japan

^e Faculty of Engineering, Academic Assembly, University of Toyama, Toyama, 930-8555, Japan

Abstract

The reaction of γ-stannylated propargyl esters in the presence of a cationic gold(I) catalyst affords vinylidenecyclopropane derivatives as a mixture of diastereomers. The cis-geometry of the alkenes is almost entirely retained in the product. DFT calculations suggest the involvement of the gold(I)-stabilized propargyl cation as a resonance form of gold(I)-coordinated allenylidene species.

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Article information

DOI: https://doi.org/10.1039/D4CC04384G
Article type: Communication
Submitted: 27 Aug 2024
Accepted: 05 Oct 2024
First published: 07 Oct 2024

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Chem. Commun., 2024,60, 13518-13521

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Synthesis of vinylidenecyclopropanes via gold(I)-catalyzed cyclopropanation of vinyl arenes with γ-stannylated propargyl esters

H. Mori, Y. Ono, S. Nakagawa, S. Akima, M. Murakami, T. Korenaga, T. Nakaji-Hirabayashi, M. Kyogoku and Y. Horino, Chem. Commun., 2024, 60, 13518 DOI: 10.1039/D4CC04384G

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Chemical Communications

Synthesis of vinylidenecyclopropanes via gold(i)-catalyzed cyclopropanation of vinyl arenes with γ-stannylated propargyl esters†

Abstract

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Synthesis of vinylidenecyclopropanes via gold(I)-catalyzed cyclopropanation of vinyl arenes with γ-stannylated propargyl esters

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