Studies on the Resolution and Absolute Configuration of cis-2- Phenylcycloheptanol

• Main Authors: Yong, Shyh-Parn, 楊士磐
• Other Authors: Shihn-Sheng Wu
• Format: Others
• Language: zh-TW
• Published: 1996
• Online Access: http://ndltd.ncl.edu.tw/handle/00821715541970085652

碩士 === 高雄醫學院 === 藥學研究所 === 84 === 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.