臺灣博碩士論文加值系統

應用 N-carbobenzoxy-L-phenylalanine (N-CBZ-L-Phe) 及 N-
carbobenzoxy- D-phenylalanine (N-CBZ-D-Phe) 對 (±)-cis-2-
phenylcycloheptanol 進行分割， 經過簡單的再結晶步驟即可分割得到
光學純度大於 98% e.e. 的左旋 (-)- 及右旋 (+)- 非鏡像異構性酯。此
兩個具高光學純度的酯類再經水解，可分別得到比旋光度 為 -93.7 的
(-)-cis-2-phenylcycloheptanol 和 +94.4 的 (+)-cis-2-phenyl-
cycloheptanol。 其後並運用 Prelog rule 來決定 (-)-cis-2-
phenylcycloheptanol 的絕對組 態 (absolute configuration) 為
(1R,2R)，而其鏡像異構物 (+)-cis-2-phenyl- cycloheptanol 可推論出
絕對組態為 (1S,2S)。我們將會用此具七圓環基團 (cyclo- heptyl-
base) 的光學輔助劑，來進行一些不齊合成 (asymmetric synthesis) 反
應的運用。

The N-carbobenzoxy-L-phenylalanine (N-CBZ-L-Phe) and N-
carbobenzoxy-D-phenylalanine (N-CBZ-D-Phe) were applied to the
optical resolution of (±)-cis-2-phenylcycloheptanol. The
resolution of (+)- and (-)-diastereomeric esters was obtained
with high optical purity (>98 % e.e.) by
simplerecrystallization. The target esters were hydrolysis to
(-)-cis-2-phenyl-cycloheptanol with [α] -93.7 and (+)-cis-2-
phenylcycloheptanol with [α] +94.4. The absolute
configuration of (-)-cis-2-phenylcycloheptanol and (+)-cis-2-
phenylcycloheptanol were determined as (1R,2R) and (1S,2S),
respectively, by using the Prelog rule. Further application on
the asymmetricsynthesis of the cycloheptyl-based chiral
auxiliary will be investigated.