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Synlett 1994; 1994(9): 741-742
DOI: 10.1055/s-1994-22993
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Diels-Alder Reaction of 3,5-Dihydro-1H-thieno[3,4-c]pyrrole 2,2-Dioxides with Alkene Dienophiles; Facile Preparation of 4,5,6,7-Tetrahydroisoindoles

Kaori Ando* , Mutsuo Kankake, Takayoshi Suzuki, Hiroaki Takayama
  • *Faculty of Pharmaceutical Sciences, Teikyo University, Sagamiko, Kanagawa 199-01, Japan
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Publication Date:
18 September 2002 (online)

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3,5-Dihydro-1H-thieno[3,4-c]pyrrole 2,2-dioxides 3 when heated with alkene dienophiles sequentially underwent a Diels-Alder reaction on the pyrrole moiety, a cheletropic elimination of sulfur dioxide, a Diels-Alder reaction of the resulting diene, and a retro Diels-Alder reaction to give 4,5,6, 7-tetrahydroisoindoles 7-9 in excellent yields.

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