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Asymmetric Alkylation of N-Toluenesulfonylimines with Dialkylzinc Reagents Catalyzed by Copper-Chiral Amidophosphine

Takahiro Soeta, Kazushige Nagai, Hidetaka Fujihara, Masami Kuriyama and Kiyoshi Tomioka*

*Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan, Email: tomiokapharm.kyoto-u.ac.jp

T. Soeta, K. Nagai, H. Fujihara, M. Kuriyama, K. Tomioka, J. Org. Chem., 2003, 59, 9655-9659.

DOI: 10.1021/jo035234q


Abstract

Various N-toluenesulfonylimines were successfully ethylated with diethylzinc in the presence of copper(II) ditriflate and a chiral amidophosphine ligand in toluene to give the corresponding N-toluenesulfonylamides in good yields and high enantioselectivity.

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Copper-Amidophosphine Catalyst in Asymmetric Addition of Organozinc to Imines

H. Fujihara, K. Nagai, K. Tomioka, J. Am. Chem. Soc., 2000, 122, 12055-12059.


Key Words

benzylamines, alkylamines


ID: J42-Y2003-940