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

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Takahiro Nishimura, Yuichi Yasuhara, and Tamio Hayashi*

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

Org. Lett., 2006, 8 (5), pp 979–981

DOI: 10.1021/ol060213e

Publication Date (Web): February 10, 2006

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 a chiral diene, (R,R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene (Ph-bod*), catalyzed the asymmetric addition of dimethylzinc to N-tosylarylimines to give high yields of chiral 1-aryl-1-ethylamines with high enantioselectivity (94−98% ee).

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Published In Issue March 02, 2006
Received January 25, 2006

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Letter

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