Isomerization of Olefins Triggered by Rhodium-Catalyzed C-H Bond Activation: Control of Endocyclic beta-Hydrogen Elimination



Yip, YY and Aissa, Christophe ORCID: 0000-0003-0750-9435
(2015) Isomerization of Olefins Triggered by Rhodium-Catalyzed C-H Bond Activation: Control of Endocyclic beta-Hydrogen Elimination. Angewandte Chemie International Edition, 54 (23). 6870 - 6873.

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Abstract

Five‐membered metallacycles are typically reluctant to undergo endocyclic β‐hydrogen elimination. The rhodium‐catalyzed isomerization of 4‐pentenals into 3‐pentenals occurs through this elementary step and cleavage of two CH bonds, as supported by deuterium‐labeling studies. The reaction proceeds without decarbonylation, leads to trans olefins exclusively, and tolerates other olefins normally prone to isomerization. Endocyclic β‐hydrogen elimination can also be controlled in an enantiodivergent reaction on a racemic mixture.

Item Type: Article
Uncontrolled Keywords: C-H activation, isomerization, metallacycles, rhodium, beta-H elimination
Subjects: ?? QD ??
Depositing User: Symplectic Admin
Date Deposited: 22 Jul 2015 10:54
Last Modified: 05 Aug 2021 16:10
DOI: 10.1002/anie.201500596
URI: https://livrepository.liverpool.ac.uk/id/eprint/2017085