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Synfacts 2010(11): 1319-1319  
DOI: 10.1055/s-0030-1258826
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Ring Opening of a Resin-Bound Chiral Aziridine with Phenols

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Chung Keun Jin
L. K. Ottesen, J. W. Jaroszewski, H. Franzyk*
University of Copenhagen, Denmark
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Publication History

Publication Date:
21 October 2010 (online)

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Significance

The resin-bound chiral aziridine 3 was prepared from polystyrene trityl bromide resin 1 with (S)-N-nosylaziridine-2-methanol (2) and used for the synthesis of coumaryl amino acids via aziridine ring opening with phenolic nucleophiles. Thus, the ring opening of aziridines was carried out with 7-hydroxycoumarins 6a-c and t-BuOK to give the corresponding aryl alkyl ethers 7a-c, which were converted into the corresponding coumaryl amino acids 9a-c in four steps in 72-93% yield.