Regioselective Functionalization of the Methylene Group Adjacent to Cyclopropyl Sulfide via Mercury(II)-Mediated Regioselective Ring-Opening Reaction

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概要

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• A regioselective bond-cleavage of the cyclopropyl sulfide (2) was performed with mercury(II) salt to supply the homoallyl anion synthon (3) bearing two reactive sites at the α and δ positions. The reaction of 3 with n-Bu_3SnH and I_2 gave α-functionalized products (8 and 9,respectively). On the other hand, recyclization of 3 into δ-functionalized cyclopropyl sulfides (2,12,13) was accomplished by treatment with several electrophiles (H^+, D^+, allyl iodide).Moreover, the synthesis of δ-oxygenated cyclopropyl sulfide (15) was achieved by the additive Pummerer reaction of the γ, δ-unsaturated γ-sulfinyl alkylmercury chloride (14) which was obtained by m-chloroperbenzoic acid oxidation of 3.

• 公益社団法人日本薬学会の論文
• 1995-11-15

著者

• 竹本 佳司

  Faculty Of Pharmaceutical Sciences Osaka University

• 岩田 宙造

  Faculty of Pharmaceutical Sciences, Osaka University

• 岩田 宙造

  阪大院薬

• 邑楽 泰一

  Faculty of Pharmaceutical Sciences, Osaka University

• Takemoto Yoshiji

  Faculty Of Pharmaceutical Sciences Osaka University

• Takemoto Y

  Graduate School Of Pharmaceutical Sciences Kyoto University

• 岩田 宙造

  Faculty Of Pharmaceutical Sciences Osaka University

• 米徳 康博

  Faculty of Pharmaceutical Sciences, Osaka University

• Ohra T

  Faculty Of Pharmaceutical Sciences Osaka University

• 邑楽 泰一

  Faculty Of Pharmaceutical Sciences Osaka University

• 米徳 康博

  Faculty Of Pharmaceutical Sciences Osaka University

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