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Synfacts 2009(8): 0926-0926  
DOI: 10.1055/s-0029-1217493
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Michael Reaction in Water Using MPS-Supported Prolinol Catalyst

Contributor(s): Yasuhiro Uozumi, Toshimasa Suzuka
Y. Chuan, G. Chen, Y. Peng*
Southwest University, Chongqing, P. R. of China
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Publication History

Publication Date:
23 July 2009 (online)

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Significance

An MPS-supported prolinol tert-butyldiphenylsilyl ether was prepared and applied to the asymmetric Michael addition reaction. Thus, immobilization of N-Boc-l-prolinol derivative 1 on MP-sulfonyl chloride resin 2 followed by deprotection of the Boc group afforded the polystyrene-supported prolinol silyl ether 4 (prolinol silyl ether loading = 0.58 mmol/g). The asymmetric Michael addition reaction of cyclohexanone to nitrostyrene was carried out in the presence of 10 mol% of catalyst 4 to give the Michael adduct in 84% yield with high stereoselectivity (90% ee, 94% de).