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

Author

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

Subjects
CYCLOPROPANATION, GOLD, ESTERS, AROMATIC compounds, RESONANCE
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. [ABSTRACT FROM AUTHOR]

Published
2024
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