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Journal article

Regioselective and Stereoselective Thioamination of 7-Oxabicyclo[2.2.1]Hept-5-En-2-Yl Derivatives

Under acidic conditions (1RS,2SR,4RS,5RS,6SR-6-exo-cyano-3-thiobenzoyl-8-oxa-3-azatricyclo[3.2.1 .0(2,4)]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-thiatricyc lo[5.2.1.0(2,6)]dec-4-en-3-endo-9-yl acetate. The latter compound was transformed into 4beta-bromo-3abeta,4,5,6,7,7abeta-hexahydro-2-phenyl-1,3-benzothiazol-6b eta, 7alpha-diyl diacetate.

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