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Article

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

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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

J. Org. Chem., 2004, 69 (20), pp 6679–6687

DOI: 10.1021/jo049469t

Publication Date (Web): September 4, 2004

To whom correspondence should be addressed. Tel: +81-43-290-3385. Fax: +81-43-290-3401.

, tmino@faculty.chiba-u.jp

Abstract

A series of novel chiral aminophosphine ligands are designed and readily prepared from (S)-prolinol. The reactivity and selectivity in the palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate with a dimethyl malonate−BSA−LiOAc system using these chiral ligands are evaluated, and the structural elucidation of ligands and palladium complex is also conducted. Moreover, a series of trialkylsilylated chiral aminophosphine ligands are prepared and applied to palladium-catalyzed asymmetric allylic alkylation (up to 98% ee).

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Published In Issue October 01, 2004
Received March 31, 2004

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Article

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

Abstract

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History

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Related Content

Asymmetric Transition Metal-Catalyzed Allylic Alkylations

Amination of N-Aryl Prolinol via Ring Expansion and Contraction: Application to the Chiral Ligand for the Catalytic Asymmetric Reaction

Asymmetric Allylic Alkylation, an Enabling Methodology

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