Synlett 1996; 1996(5): 461-464
DOI: 10.1055/s-1996-5446
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Lewis Acid-Catalysed Oxidative Cycloaddition of Thiophenes1

Yuanqiang Li, Michio Matsuda, Thies Thiemann1 , Tsuyoshi Sawada, Shuntaro Matake, Masashi Tashiro2
  • 1Lab. de Química Farmacêutica, Faculdade de Farmácia, Universidade de Coimbra, 3000 Coimbra, Portugal
  • 2Institute of Advanced Material Study, 6-1, Kasuga-koh-en, Kasuga-shi, Fukuoka 816, Japan
Further Information

Publication History

Publication Date:
31 December 2000 (online)

Thiophenes 1 have been treated with m-CPBA under BF3⋅Et2O catalysis. The thiophene-S-monoxides intermediary produced have been reacted in situ with various dienophiles. It could be shown that Lewis acid catalysis enhances the yield of the oxidative cycloaddition of thiophenes considerably. Moreover a greater variety of dienophiles can be used in the corresponding uncatalysed reaction. Thiophene-S-monoxides have also been isolated and subjected to subsequent cycloaddition in a two-step procedure.