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Synlett 1991; 1991(7): 469-471
DOI: 10.1055/s-1991-20763
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Highly Stereoselective Synthesis of (±)-Aminobromocyclitol Derivatives from Furan

Erika Reynard* , Jean-Louis Reymond, Pierre Vogel
  • *Section de chimie de l'Université, 2 rue de la Barre, CH-1005 Lausanne, Switzerland
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Publication Date:
07 March 2002 (online)

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The Diels-Alder adduct (2-cyano-7-oxabicyclo[2.2.1]-hept-5-en-2-yl acetate) of furan and 1-cyanovinyl acetate was converted to N-[(1RS,2RS,3RS,4SR, 6RS)-2,3,4-triacetoxy-6-bromocyclohex-1-yl]benzamide and to N-[(1RS, 2RS,3SR,4RS,5SR,6SR)-2,3,4,5-tetraacetoxy-6-bromocyclohex-1-yl]benzamide with high stereoselectivity.