中文摘要
本論文係利用酵素製備高純度鏡像化合物(-)-2-(1-naphthyl)cyclohexan-1-ol及(+)-2-(1-naphthyl)cyclohexan-1-ol。經過多次實驗條件的改良，並利用高效能液相層析儀追蹤反應及結果分析後，可得最佳分離條件為：酵素種類為lipase AK；酵素與起始物(+)-2-(1-naphthyl)cyclohexan-1-ol重量比為2：1；所使用的酯化試劑為Vinyl acetate，與起始物莫耳數比為10：1；反應溫度為35℃；反應時間為5日，利用這樣的條件分離即可達到兩者純度皆高於99%。而我們將利用酵素進行分離反應所得到鏡像化合物輔助基進行氰基酯化合物之烷化反應，以探討對α-碳立體位向的選擇性。當進行雙取代烷化反應，所用之烷化試劑的立體結構較大時，如溴化甲苯，經由動力學控制，所得到的位向選擇性較立體結構小的烷化試劑高。這些研究內容的說明，將詳述於本論文中。

Abstract
In 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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