Asymmetric Synthesis of Optically Active 3-Substituted δ-Valerolactones Using Lipase in Organic Solvents(Organic Chemistry)
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概要
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In organic solvents, lipase Amano P catalyzed the asymmetric ring opening of glutaric anhydrides bearing CH_2Cl, -CH_2F and OCH_3 groups at position 3 with methanol and 1-butanol to afford the corresponding mono esters in 70-86% e.e. Optically active δ-valerolactones were synthesized from the mono esters in overall yields of 34-62%. The ^-configuration was assigned to the mono esters and the lactones by means of a CD analysis and chemical correlation. This indicates that the lipase preferentially attacked the pro-R carbonyl group of these anhydrides carrying hetero atoms, in keeping with the trend observed for glutaric anhydrides having simple alkyl substituents.
- 社団法人日本農芸化学会の論文
著者
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Sawada Seiji
Department Of Chemistry Kyoto University Of Education
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YAMAMOTO Yukio
Departments of Microbiology, Hamamatsu Medical Center
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IWASA Mineyuki
Department of Chemistry, Kyoto University of Education
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Iwasa Mineyuki
Department Of Chemistry Kyoto University Of Education
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Yamamoto Yukio
Department Of Agricultural Chemistry Faculty Of Agriculture Nagoya University
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Yamamoto Yukio
Department Of Chemistry College Of Liberal Arts And Sciences Kyoto University
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