立体化学の研究(第56報)(Acetylacetonato)[(1R, 2S)-N-alkylephedrinato]-dioxomolybdenumを不斉触媒とするアリルアルコールの不斉エポキシ化反応

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概要

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• The catalytic asymmetric epoxidation of allylic alcohols (2a-c) with alkyl hydro-peroxides (4a, b) was attempted using chiral oxidation catalysts, (acetylacetonato)-[(1R, 2S)-N-alkylephedrinato] dioxomolybdenum (1a-c). Examination of factors, including reaction temperature, solvent, nature of oxidants, and amount of catalyst, which may affect both the chemical and optical yields of optically active 2,3-epoxy alcohols (3a-c), resulted in the establishment of the optimal reaction condition for asymmetric epoxidation. Based on these results, the preparation of 3a-c having a (2R)-configuration was achieved with a maximum optical yield of 33% ee. The absolute configurations and optical purity of 3a-c were determined by chemical correlation with (R)-3-methylbutane-1,2,3-triol (8), (R)- and (S)-linalool (11 and 14), respectively. The epoxidation mechanism is discussed in detail.

• 社団法人日本薬学会の論文
• 1980-03-25

著者

• 山田 俊一

  東京大学

• 山田 俊一

  東京大学薬学部

• 寺島 孜郎

  (財)相模中央化学研究所

• 益子 敏夫

  東京大学薬学部

• 寺島 孜郎

  東京大学薬学部

• 寺島 孜郎

  Faculty Of Pharmaceutical Sciences University Of Tokyo:(present Address)sagami Chemical Research Cen

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