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利用脂肪分解酵素(Lipase AK)以製備具高光學純度之(+)-及(-)-2-芳香基環己醇並應用於掌性α-氰基酯化合物之烷化反應研究
Thesis

利用脂肪分解酵素(Lipase AK)以製備具高光學純度之(+)-及(-)-2-芳香基環己醇並應用於掌性α-氰基酯化合物之烷化反應研究

吳晨帆
Masters, National Tsing Hua University
2002

Abstract

脂肪分解酵素芳香基環己醇掌性α-氰基酯化合物烷化反應 Lipase AK( + )-2-Arylcyclohexanols(-)-2-ArylcyclohexanolsChiral AuxilariesAsymmetric Alkylationa-Cyano EstersKinetic Resolution
AbstractIn this thesis, we like to discuss the efficient utility of the enzyme lipase AK to separate the optical antipodes (-)-2-and (+)-2-(1-naphthyl)cyclohexan-1-ol from its racemic mixture. By varying the reaction condition, the best experimental condition appeared to be the enzyme to alcohol ratio 2 : 1(by weight) and we use HPLC as the tool to separate it and after separation we duly analysed the result so obtained. In a typical procedure, the racemic alcohol and vinyl acetate were taken in the ratio of 10 : 1(by mole) and to this mixture was added the enzyme, lipase AK in t-BuOMe at 35℃, and the resulting mixture was stirred for 5 days. Taking optically pure alcohol as the chiral auxiliary, we also carried out the C-alkylation reaction of a-cyano ester and like to see the enantioselectivity, we also like to see the stereoselectivity outcome of a reaction by changing the aromatic part of the chiral auxiliary and also changing the reaction condition viz-temperature. In this context, we like to mention that when alkylation reaction was carried out with larger alkylating agent like benzyl bromide, we got higher diastereoselectivity 2 : 1. The detailed will be explained in this thesis.

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