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Synfacts 2007(5): 0503-0503  
DOI: 10.1055/s-2007-968455
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Kinetic Resolution of 1,3-Cyclohexadiene Epoxide with Grignards

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
R. Millet, A. Alexakis*
University of Geneva, Switzerland
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Publikationsdatum:
24. April 2007 (online)

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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 SN2′ pathway. Various primary and secondary Grignard reagents worked well in the resolution, giving ee values in the range of 64-90% ee.