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Synfacts 2011(1): 0117-0117  
DOI: 10.1055/s-0030-1259144
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Polystyrene-Supported Chiral Auxiliary for Asymmetric Alkylation

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Shaheen M. Sarkar
F.-Q. Hu, D.-X. Xia, C.-F. Lu, Z.-X. Chen, G.-C. Yang*
Hubei University, Wuhan, P. R. of China
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Publikationsverlauf

Publikationsdatum:
21. Dezember 2010 (online)

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Significance

A non-cross-linked polystyrene (NCPS) supported 2-phenylimino-2-oxazolidine chiral auxiliary (4) was prepared for the asymmetric α-alkylation of carbonyl compounds. Thus, the asymmetric alkylation of polymeric amides 5 prepared from 4 was performed with LDA and alkyl bromides followed by treatment with benzyl amine to give the corresponding optically active N-benzyl amides 7 in 63-69% yield with 96-99% ee (6 examples). NCPS-supported chiral auxiliary 4 was readily recovered and reused four times.