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Synlett 2001; 2001(Special Issue): 0995-0998
DOI: 10.1055/s-2001-14644
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Diastereoselective Synthesis of Diamino 1,2-Diols from Homochiral α-Aminoacylsilanes

Bianca F. Bonini* , Mauro Comes-Franchini, Mariafrancesca Fochi, Lodovico Lunazzi, Andrea Mazzanti, Germana Mazzanti, Alfredo Ricci, Greta Varchi
  • *Dipartimento di Chimica Organica "A. Mangini", Università di Bologna, Viale Risorgimento 4, 40136-Bologna, Italy; Fax + 39 51 2 09 36 54; E-mail: ricci@ms.fci.unibo.it
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Publication Date:
31 December 2001 (online)

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We have developed a new synthetic access to stereodefined diamino 1,2-diols starting from homochiral α-aminoacylsilanes. A [3 + 2] cycloaddition with benzo nitrile oxide of the vinylated adducts and a reductive ring opening constitute key steps of the reaction sequence.

α-aminoacylsilanes - vinylation - dipolar cycloaddition - aminopolyols