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Synlett 1994; 1994(4): 282-284
DOI: 10.1055/s-1994-22829
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Chiral Acyclic Nitrone Bearing Protected Vicinal Diol Controller Providing Single π(C=N)-Face in [3+2] Cycloaddition Reactions

Seiki Saito* , Teruhiko Ishikawa, Norihisa Kishimoto, Tomonari Kohara, Toshio Moriwake
  • *Department of Applied Chemistry, Faculty of Engineering, Okayama University, Tsushima, Okayama 700, Japan
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Publication Date:
22 March 2002 (online)

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Acyclic chiral (Z)-nitrone (4) bearing the protected vicinal diol controller has been developed with the intention of shielding one of its π-(C=N) diastereofaces. The intermolecular [3+2] cycloaddition reactions of 4 with various olefins resulted in perfect discrimination of the nitrone faces though that of the olefins depended on their structures.