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Synlett 1994; 1994(4): 279-281
DOI: 10.1055/s-1994-22828
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Role of Vicinal Diol Controller in Discriminating π(C=C)-Faces of Dipolarophile in Nitrone-Olefin Cycloaddition Reactions

Seiki Saito* , Teruhiko Ishikawa, 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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Diastereofaces of carbon-carbon double bonds linked to (4S,5S)-bis(t-butyldimethylsiloxy)-framework as a controller of acyclic conformation have been differentiated with >99 %de in nitrone-olefin [3+2] cycloaddition reactions, whereas the nitrones were discriminated with selectivity ranging from 60 to 88 %de.