C2-Symmetric Bicyclo[2.2.2]octadienes as Chiral Ligands: Their High Performance in Rhodium-Catalyzed Asymmetric Arylation of N-Tosylarylimines

Norihito Tokunaga, Yusuke Otomaru, Kazuhiro Okamoto, Kazuhito Ueyama, Ryo Shintani and Tamio Hayashi*

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

N. Tokunaga, Y. Otomaru, K. Okamoto, K. Ueyama, R. Shintani, T. Hayashi, J. Am. Chem. Soc., 2004, 126, 13584-13585.

DOI: 10.1021/ja044790e (free Supporting Information)

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Abstract

The use of a new C₂-symmetric diene ligand (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene (Ph-bod*) for the rhodium-catalyzed asymmetric arylation of N-tosylarylimines with arylboroxines allowed asymmetric synthesis of diarylmethylamines with high enantioselectivity.

see article for more examples

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Asymmetric Addition of Dimethylzinc to N-Tosylarylimines Catalyzed by a Rhodium-Diene Complex toward the Synthesis of Chiral 1-Arylethylamines

T. Nishimura, Y. Yasuhara, T. Hayashi, Org. Lett., 2006, 8, 979-981.

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Key Words

Diarylmethylamines

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ID: J48-Y2004-1770