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Synfacts 2005(1): 0170-0170  
DOI: 10.1055/s-2005-872219
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Polymer-Supported Acetylating Agent for the Kinetic Resolution of Amines

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Takayasu Arakawa
S. Arseniyadis, P. V. Subhash, A. Valleix, A. Wagner*, C. Mioskowski*
Université Louis Pasteur de Strasbourg, France
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Publication History

Publication Date:
21 September 2005 (online)

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Significance

A recyclable polymer-supported enantioselective acetylating agent (1) for the kinetic resolution of amines was prepared from chloromethylated polystyrene in four steps. The enantioselective N-acetylation of ()-1-phenylethyl­-amine was performed at room temperature with 0.2 molar equivalent of 1 to give 82% ee of (R)-N-1-phenylethylacetamide. Four examples of kinetic resolution of various amines were demonstrated to afford the corresponding acetamides with 69-82% enantiomeric purities (yields: no information).