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Letter

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

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Fu-Xue Chen, Asato Kina, and Tamio Hayashi*

Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan

Org. Lett., 2006, 8 (2), pp 341–344

DOI: 10.1021/ol052756e

Publication Date (Web): December 24, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, thayashi@kuchem.kyoto-u.ac.jp

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 cyclic α,β-unsaturated ketones, 0.005−0.01 mol % of the catalyst giving high yields of the addition products with not lower than 94% ee. The turnover frequency of the catalyst is up to 1.4 × 10⁴ h^-¹.

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Published In Issue January 19, 2006
Received November 14, 2005

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Letter

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

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Rhodium-Catalyzed Asymmetric 1,4-Addition of Aryl- and Alkenylboronic Acids to Enones

Chiral [2.2.2] Dienes as Ligands for Rh(I) in Conjugate Additions of Boronic Acids to a Wide Range of Acceptors

Chiral Phosphine−Olefin Ligands in the Rhodium-Catalyzed Asymmetric 1,4-Addition Reactions

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