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Synthesis 1991; 1991(11): 923-928
DOI: 10.1055/s-1991-26607
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Highly Stereoselective Aminohydroxylations of exo-2-Cyano-7-oxabicyclo[2.2.1]hept-5-en-2-yl Acetate

Susy Allemann* , Pierre Vogel
  • *Section de chimie de I'Université de Lausanne,2, rue de la Barre, CH-1005 Lausanne, Switzerland
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Publikationsdatum:
29. April 2002 (online)

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Protected forms of exo-5-amino-exo-6-hydroxy-7-oxabicyclo [2.2.1]heptan-2-one and of exo-5-amino-endo-6-hydroxy-7-oxabicyclo [2.2.1]heptan-2-one can be obtained readily and with high stereoselectivity from exo-2-cyano-7-oxabicyclo[2.2.1] hept-5-en-2-yl acetate (±)-(7). The processes involve acid promoted rearrangements of N-carbonyl aziridines 10 [(1 RS, 2SR, 4RS,5RS,6SR)-6-cyano-8-oxa-3-azatricyclo[3.2.1.02,4] oct-6-yl acetate derivatives] derived from (±)-7.