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Synlett 1993; 1993(6): 395-396
DOI: 10.1055/s-1993-22467
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Asymmetric 1,3-Dipolar Cycloaddition of Cyclic Nitrones to Crotonic Acid Derivatives Bearing Chiral Auxiliaries. Synthesis of Optically Active ß-Amino Acids, (+)-Sedridine, and (+)-Hygroline

Shun-Ichi Murahashi* , Yasushi Imada, Masahiko Kohno, Toru Kawakami
  • *Department of Chemistry, Faculty of Engineering Science, Osaka University, Machikaneyama, Toyonaka, Osaka 560, Japan
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Publication Date:
19 March 2002 (online)

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Asymmetric 1,3-dipolar cycloaddition of cyclic nitrones with optically active crotonic acid derivatives bearing chiral auxiliaries in the presence of zinc iodide gives bicyclic isoxazolidines, which are precursors of ß-amino acids, highly stereoselectively. By using these reactions (+)-sedridine (4) and (+)-hygroline (5) can be synthesized readily.