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Development of Chiral (S)-Prolinol-Derived Ligands for Palladium-Catalyzed Asymmetric Allylic Alkylation: Effect of a Siloxymethyl Group on the Pyrrolidine Backbone

Youichi Tanaka, Takashi Mino,* Koji Akita, Masami Sakamoto and Tsutomu Fujita

*Department of Materials Technology, Faculty of Engineering, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan, Email: tminofaculty.chiba-u.jp

Y. Tanaka, T. Mino, K. Akita, M. Sakamoto, T. Fujita, J. Org. Chem., 2004, 69, 6679-6687.

DOI: 10.1021/jo049469t (free Supporting Information)


Abstract

A series of trialkylsilylated chiral aminophosphine ligands are prepared from (S)-prolinol and applied to a palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate with a dimethyl malonate-BSA-LiOAc system.

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Key Words

Allylation, Benzylation, Tsuji-Trost Reaction


ID: J42-Y2004-1260