Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2010(3): 0369-0369
DOI: 10.1055/s-0029-1219288
DOI: 10.1055/s-0029-1219288
Polymer-Supported Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Michael Addition with a Polymer-Supported Organocatalyst
E. Alza, M. A. Pericàs*
Institute of Chemical Research of Catalonia, Tarragona and Universitat de Barcelona, Spain
Further Information
Publication History
Publication Date:
18 February 2010 (online)
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).