High Performance of a Chiral Diene-Rhodium Catalyst for the Asymmetric 1,4-Addition of Arylboroxines to α,β-Unsaturated Ketones

Fu-Xue Chen, Asato Kina and Tamio Hayashi*

*Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan, Email: thayashikuchem.kyoto-u.ac.jp

F.-X. Chen, A. Kina, T. Hayashi, Org. Lett., 2006, 8, 341-344.

DOI: 10.1021/ol052756e

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Abstract

A rhodium complex coordinated with (S,S)-2,5-dibenzylbicyclo[2.2.2]octa-2,5-diene (Bn-bod*) showed high catalytic activity and high enantioselectivity in the asymmetric 1,4-addition of arylboroxines to α,β-unsaturated ketones. It is suggested, that phenylboronic acid contains a small amount of a contaminant which deactivates the catalyst. This impurity was removed during the preparation and purification of the boroxines.

see article for more examples

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Simple Chiral Diene Ligands Provide High Enantioselectivities in Transition-Metal-Catalyzed Conjugate Addition Reactions

K. Okamoto, T. Hayashi, V. H. Rawal, Org. Lett., 2008, 10, 4387-4389.

A Chiral Chelating Diene as a New Type of Chiral Ligand for Transition Metal Catalysts: Its Preparation and Use for the Rhodium-Catalyzed Asymmetric 1,4-Addition

T. Hayashi, K. Ueyama, N. Tokunaga, K. Yoshida, J. Am. Chem. Soc., 2003, 125, 11508-11509.

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Key Words

Conjugate Addition

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ID: J54-Y2006-300