Recent advances in the metal-catalyzed asymmetric alkene hydrogenation of cyclic conjugated carbonyl compounds

Tan, Min; Peters, Bram B. C.; Andersson, Pher G.; Zhou, Taigang

doi:10.1039/d4qo00227j

Org. Chem. Front.

2024

DOI: 10.1039/d4qo00227j

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Recent advances in the metal-catalyzed asymmetric alkene hydrogenation of cyclic conjugated carbonyl compounds

Min Tan,

Bram B. C. Peters,

Pher G. Andersson

et al.

Abstract: The transition metal catalyzed asymmetric hydrogenation of carbon-carbon double bonds is recognized as one of the most straightforward methods for the preparation of stereopure compounds. Chiral cyclic motifs have widespread...

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2024

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Asymmetric and Chemoselective Iridium Catalyzed Hydrogenation of Conjugated Unsaturated Oxime Ethers

Zhao,

Peters,

Zhang

et al. 2024

Chemistry A European J

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Research on the chemoselective metal‐catalyzed hydrogenation of conjugated p‐systems has mostly been focussed on enones. Herein, we communicate the understudied asymmetric hydrogenation of enimines catalyzed by N,P‐iridium complexes and chemoselective toward the alkene. A number of enoxime ethers underwent hydrogenation smoothly to yield the desired products in high yield and stereopurity (up to 99% yield, up to 99% ee). No hydrogenation of the C=N p‐bond was observed under the applied reaction conditions (20 bar H2, rt, DCM). It was demonstrated that the chiral oxime ether could be hydrolyzed into the ketone with complete preservation of the installed stereogenity at the α‐carbon. At last, a binding mode of the substrate to the active iridium catalyst and the consequence for the stereoselective outcome was proposed.

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Asymmetric and Chemoselective Iridium Catalyzed Hydrogenation of Conjugated Unsaturated Oxime Ethers

Zhao,

Peters,

Zhang

et al. 2024

Chemistry A European J

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show abstract

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Recent advances in the metal-catalyzed asymmetric alkene hydrogenation of cyclic conjugated carbonyl compounds

Abstract: The transition metal catalyzed asymmetric hydrogenation of carbon-carbon double bonds is recognized as one of the most straightforward methods for the preparation of stereopure compounds. Chiral cyclic motifs have widespread...

Cited by 1 publication

References 93 publications

Asymmetric and Chemoselective Iridium Catalyzed Hydrogenation of Conjugated Unsaturated Oxime Ethers

Asymmetric and Chemoselective Iridium Catalyzed Hydrogenation of Conjugated Unsaturated Oxime Ethers

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