Stereodivergent Synthesis of Chiral 2-Alkenylaziridines : Palladium(0)-Catalyzed 2,3-cis-Selective Aziridination and Base-Mediated 2,3-trans-Selective Aziridination

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概要

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• Whereas treatment of the allylic mesylates of N-protected 2-alkyl-4-amino-(E)-2-alken-1-ols with sodium hydride in DMF yields exclusively the corresponding thermodynamically less stable 2,3-frans-2-alkenyl-3-alkylaziridines, exposure of the methyl carbonates of N-protected 2-alkyl-4-amino-(E)-2-alken-1-ols to a catalytic amount of Pd(PPh_3)_4 in THF or 1,4-dioxane affords predominantly the corresponding thermodynamically more stable 2,3-cis-2-alkenyl-3-alkylaziridines. The kinetically favored frans-selective aziridination would be attributed to the allylic 1,3-strain in aza-anionic intermediates. The conformational analysis of the sterically highly congested 2-alkenylaziridines thus obtained is also presented.

• 社団法人日本薬学会の論文
• 2004-01-01

著者

• Takemoto Yoshiji

  Graduate School Of Pharmaceutical Sciences Kyoto Univ. Yoshida Sakyo-ku Kyoto 606-8501 Jpn

• Takemoto Yoshiji

  Faculty Of Pharmaceutical Sciences Osaka University

• OHNO Hiroaki

  Graduate School of Pharmaceutical Sciences, Osaka University

• FUJII Nobutaka

  Graduate School of Pharmaceutical Sciences, Kyoto University

• TANAKA Tetsuaki

  Graduate School of Pharmaceutical Sciences, Osaka University

• IBUKA Toshiro

  Graduate School of Pharmaceutical Sciences, Kyoto University

• Ohno Hiroaki

  Graduate School Of Pharmaceutical Sciences Kyoto University

• 大野 浩章

  京都大学大学院薬学研究科

• Takemoto Yoshiji

  Graduate School Of Pharmaceutical Sciences Kyoto Univ.

• Takemoto Yoshiji

  Graduate School Of Pharmaceutical Sciences Kyoto University

• Ibuka T

  Graduate School Of Pharmaceutical Sciences Kyoto University

• Ibuka Toshiro

  Graduate School Of Pharmaceutical Sciences Kyoto University

• Fujii N

  Graduate School Of Pharmaceutical Sciences Kyoto University

• Fujii Nobutaka

  Graduate School Of Pharmaceutical Sciences Kyoto University

• Tanaka T

  Graduate School Of Pharmaceutical Sciences Osaka University

• Tanaka Tetsuaki

  Graduate School Of Pharmaceutical Sciences Of Osaka University

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