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Synfacts 2010(3): 0369-0369  
DOI: 10.1055/s-0029-1219288
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Michael Addition with a Polymer-Supported Organocatalyst

Contributor(s): Yasuhiro Uozumi, Takao Osako
E. Alza, M. A. Pericàs*
Institute of Chemical Research of Catalonia, Tarragona and Universitat de Barcelona, Spain
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Publication History

Publication Date:
18 February 2010 (online)

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Significance

A polystyrene-supported (S)-α,α-diphenylprolinol trimethylsilyl ether (6) was prepared from 1 via the Grignard alkylation, silylation with the concomitant carbamate deprotection, and the Huisgen 1,3-dipolar cycloaddition with azidomethylpolystyrene 4 (eq. 1). The polystyrene-supported organocatalyst 6 promoted the Michael addition of aldehydes to nitroolefins to give the corresponding adducts in up to 98% yield with up to >99% syn selectivity and up to >99% ee (8 examples, eq. 2).