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Synlett 1993; 1993(10): 801-803
DOI: 10.1055/s-1993-22615
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Regio- and Stereoselective Thioamination of 7-Oxabicyclo[2.2.1]hept-5-en-2-yl Derivatives

Susy Alleman* , Pierre Vogel
  • *Section de chimie de l'Université, 2 rue de la Barre, CH-1005 Lausanne, Switzerland
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Publication History

Publication Date:
19 March 2002 (online)

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Under acidic conditions (1RS,2SR,4RS, 5RS,6SR)-6-exo-cyano-3-thiobenzoyl-8-oxa-3-azatricyclo [3.2.1.02,4]oct-6-endo-yl acetate was rearranged selectively into (1RS,2RS,6RS,7RS, 9SR)-9-exo-cyano-4-phenyl-3,10-dioxa-5-aza-3- thiatricyclo[5.2.1.02,6]dec-4-en-3-endo-9-yl acetate. The latter compound was transformed into 4β-bromo-3aβ,4,5,6,7,7aβ-hexahydro-2- phenyl-1,3-benzothiazol-6β,7α-diyl diacetate.

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