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Synlett 1995; 1995(SI): 552-554
DOI: 10.1055/s-1995-5282
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Piperidine Triols via Enantioselective Alkylation and Osmylation of Alanine Schiff Base Esters

Dalibor Sames, Robin Polt*
  • *Department of Chemistry, University of Arizona, Tucson, AZ 85721, USA, Fax: (520) 621-8407, E-mail: POLT@CCIT.arizona.edu
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Publication Date:
31 December 2000 (online)

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Tandem reduction-alkenylation of Schiff base derivatives of optically pure α-amino esters, followed by catalytic osmylation of the resulting allylic threo-amino alcohols provides a facile route to galacto- and fuco-amino sugar derivatives. Subsequent cyclization (reductive amination) provides biologically interesting aza-sugar derivatives in high yield with excellent stereocontrol.

amino acids - nojirimycin - fucosidase inhibitor - selective oxidation