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Synfacts 2008(7): 0769-0769  
DOI: 10.1055/s-2008-1078443
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Microwave-Assisted Ring-Opening of Aziridines Using Resin-Bound Amines

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Chung Keun Jin
F. Crestey, M. Witt, K. Frydenvang, D. Stærk, J. W. Jaroszewski, H. Franzyk*
University of Copenhagen, Denmark and Bruker Daltonik GmbH, Bremen, Germany
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Publication History

Publication Date:
20 June 2008 (online)

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Significance

The solid-phase ring-opening of N-nosyl aziridines under microwave conditions is described. Thus, p-nitrobenzenesulfonyl (nosyl = Ns)-activated aziridines 2a-g were prepared from1,2-amino alcohols 1a-g with an excess amount of nosyl chloride (NsCl) in CH2Cl2-pyridine (2:1). The ring-opening of the aziridines 2a-g with resin-bound amines 3-5 gave the corresponding amines 6-12 in >25 to >95% yield with 63-97% purity after acidic cleavage. The glycine and proline derivatives 16-18 were also obtained from 13-15 in >95% yield with 93-97% purity.