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Synlett 1996; 1996(10): 985-986
DOI: 10.1055/s-1996-5653
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Oxygen Nucleophile Initiated Tandem Conjugate Addition Reactions of 1-Nitro-1-cyclohexene with 4-Hydroxy-2-butynoates: Synthesis of Octahydrobenzo[b]furans

Takayuki Yakura, Tomoko Tsuda, Yukiko Matsumura, Seiji Yamada, Masazumi Ikeda*
  • *Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607, Japan, Fax +81(75)595-4763
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Publication Date:
31 December 2000 (online)

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Treatment of 1-nitro-1-cyclohexene with methyl 4-hydroxy-2-butynoate in the presence of potassium tert-butoxide gave 3a-nitrooctahydrobenzo[b]furan in excellent yield through a tandem conjugate addition initiated by the oxygen nucleophile.

oxygen nucleophile - tandem conjugate addition reaction - 1-nitro-1-cyclohexene - 4-hydroxy-2-butynoate - octahydrobenzo[b]furan

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