Lipase-catalyzed Kinetic Resolution of (±)-trans- and cis-2-Azidocycloalkanols
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概要
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The lipase-catalyzed kinetic resolution of trans-and cis-2-azidocycloalkanols and the preparation of enantiomerically pure trans-and cis-2-aminocycloalkanols are described. Four kinds of lipases were screened for the acetylation of trans-and cis-2-azidocycloalkanols. Among them, Pseudomonas sp. lipases (lipase PS and lipase AK, Amamo Pharmaceutical Co.) showed the highest enantioselectivity. These products were converted to the corresponding 2-aminocycloalkanols to determine their enantiomeric excess (ee) and absolute configurations by HPLC and CD analyses, using (S)-TBMB carboxylic acid [(S)-2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylic acid] as the chiral conversion reagent. The results of the CD analysis proved N, O-bis-(S)-TBMB carboxylated cis-2-aminocycloalkanols to adopt a predominantly N-equatorial conformation. The partially resolved trans-and cis-2-aminocy-cloalkanols, except for trans-2-aminocyclopentanol, were recrystallized from ethyl acetate to give enantiomercally pure forms.
- 社団法人日本農芸化学会の論文
- 1999-12-23
著者
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OHRUI Hiroshi
Division of Applied Life Science, Graduate School of Agricultural Science, Tohoku University
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Ohrui Hiroshi
Division Of Life Science Graduate School Of Agricultural Science Tohoku University
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