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Kinetic Resolution of 1,3-Cyclohexadiene Epoxide with Grignards

A. Alexakis, Rémy T. Millet

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Abstract

Significance The authors describe the kinetic resolution of 1,3-cyclohexadiene monoepoxides under copper catalysis utilizing a chiral ferrocenyl-based ligand. Phosphoramidite N-heterocyclic carbene ligands were also tested, but failed in comparison with the ferrocenyl-type ligand. The reaction uses Grignard reagents and regioselectively proceeds via an S N 2′ pathway. Various primary and secondary Grignard reagents worked well in the resolution, giving ee values in the range of 64-90% ee.

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What this paper is about

Significance The authors describe the kinetic resolution of 1,3-cyclohexadiene monoepoxides under copper catalysis utilizing a chiral ferrocenyl-based ligand. Phosphoramidite N-heterocyclic carbene ligands were also tested, but failed in comparison with the ferrocenyl-type ligand. The reaction uses Grignard reagents and regioselectively proceeds via an S N 2′ pathway. Various primary and secondary Grignard reagents worked well in the resolution, giving ee values in the range of 64-90% ee.

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Available abstract

Significance The authors describe the kinetic resolution of 1,3-cyclohexadiene monoepoxides under copper catalysis utilizing a chiral ferrocenyl-based ligand. Phosphoramidite N-heterocyclic carbene ligands were also tested, but failed in comparison with the ferrocenyl-type ligand. The reaction uses Grignard reagents and regioselectively proceeds via an S N 2′ pathway. Various primary and secondary Grignard reagents worked well in the resolution, giving ee values in the range of 64-90% ee.

Key concepts: Kinetic resolution, Chemistry, Phosphoramidite, Ligand (biochemistry), SN2 reaction, Reagent, Resolution (logic), Combinatorial chemistry

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