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Synfacts 2006(1): 0087-0087  
DOI: 10.1055/s-2005-921701
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Polymer-Supported Methyleneaziridines for Multicomponent Reactions

Contributor(s): Yasuhiro Uozumi, Ray Kawade, Toshimasa Suzuka
J.-F. Margathe, M. Shipman*, S. C. Smith
University of Warwick and Syngenta, Jealott’s Hill International Research Centre, Bracknell, UK
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Publication History

Publication Date:
16 December 2005 (online)

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Significance

1,3-Disubstituted propanones 4 were prepared by a three-component reaction of 2-methyleneazilizines 1 anchored on the resin with Grignard reagents and electrophiles. Thus, methyleneazilizines 1 reacted with several Grignard reagents in the presence of cupper iodide to form the corresponding metalloenamines 2. The alkylation of metalloenamines 2 with alkyl electrophiles gave ketimine derivatives 3. Filtration and hydrolysis of resin-bound ketimines 3 with pH 4.5 buffer provided the corresponding 1,3-disubstituted propanones 4a-f in 39-81% yields with high purity (91-99%).