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Stereoselective Access to Conjugated and Cross-Conjugated Dienoates by Rh- and Ru-Catalyzed Isomerizations of Vinylcyclopropanes

Published inOrganic letters, vol. 24, no. 2, p. 752-756
Publication date2022-01-03
First online date2022-01-03
Abstract

Two complementary catalytic protocols for the isomerization of stereoisomeric mixtures of vinylcyclopropanes are described. A commercially available cationic rhodium complex provides access to conjugated dienoates in high yield with excellent stereocontrol. The combination of a bisphosphine ligand and a ruthenium precatalyst affords cross-conjugated dienoates via a formal 1,3-ring opening. The products are obtained with moderate to high stereoselectivity. The ability of each type of dienoate to engage in [4 + 2] cycloaddition reactions has been demonstrated.

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Citation (ISO format)
GARBO, Michele, MAZET, Clement. Stereoselective Access to Conjugated and Cross-Conjugated Dienoates by Rh- and Ru-Catalyzed Isomerizations of Vinylcyclopropanes. In: Organic letters, 2022, vol. 24, n° 2, p. 752–756. doi: 10.1021/acs.orglett.1c04223
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ISSN of the journal1523-7052
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Creation01/21/2022 10:33:00 AM
First validation01/21/2022 10:33:00 AM
Update time03/16/2023 2:27:45 AM
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