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Desymmetrization of σ-Symmetric Biphenyl-2,6-diyl Diacetate Derivatives by Lipase-Catalyzed Hydrolysis: Unexpected Effect of C(3′)-Substituent on the Enantiotopic Group Selectivity
Synlett ( IF 1.7 ) Pub Date : 2019-01-04 , DOI: 10.1055/s-0037-1611701 Takashi Matsumoto , Mio Ochiai , Yuki Akisawa , Daichi Kajiyama
Synlett ( IF 1.7 ) Pub Date : 2019-01-04 , DOI: 10.1055/s-0037-1611701 Takashi Matsumoto , Mio Ochiai , Yuki Akisawa , Daichi Kajiyama
Highly enantioselective desymmetrization of σ-symmetric 3′-substituted 2′,6′-dimethoxybiphenyl-2,6-diyl diacetate derivatives to the corresponding monoacetates was effected by using Rhizopus oryzae lipase (ROL) and porcine pancreatic lipase (PPL), despite the remoteness of the C(3′) substituent from the acetate groups. ROL promoted hydrolysis of the pro-S acetates, irrespective of the type of C(3′) substituent, whereas PPL promoted hydrolysis of the pro-R acetates, and selectivity was only attainable when the C(3′) substituent was a polar group.
中文翻译:
σ-对称联苯-2,6-二乙酸二酯衍生物通过脂肪酶催化水解去对称化:C(3')-取代基对对映基团选择性的意外影响
使用米根霉脂肪酶 (ROL) 和猪胰脂肪酶 (PPL) 将 σ 对称 3'-取代的 2',6'-二甲氧基联苯-2,6-二基二乙酸酯衍生物高度对映选择性去对称化为相应的单乙酸酯,尽管C(3') 取代基远离乙酸酯基团。ROL 促进 pro-S 乙酸酯的水解,与 C(3') 取代基的类型无关,而 PPL 促进 pro-R 乙酸酯的水解,只有当 C(3') 取代基是极性基团时才能达到选择性.
更新日期:2019-01-04
中文翻译:
![](https://scdn.x-mol.com/jcss/images/paperTranslation.png)
σ-对称联苯-2,6-二乙酸二酯衍生物通过脂肪酶催化水解去对称化:C(3')-取代基对对映基团选择性的意外影响
使用米根霉脂肪酶 (ROL) 和猪胰脂肪酶 (PPL) 将 σ 对称 3'-取代的 2',6'-二甲氧基联苯-2,6-二基二乙酸酯衍生物高度对映选择性去对称化为相应的单乙酸酯,尽管C(3') 取代基远离乙酸酯基团。ROL 促进 pro-S 乙酸酯的水解,与 C(3') 取代基的类型无关,而 PPL 促进 pro-R 乙酸酯的水解,只有当 C(3') 取代基是极性基团时才能达到选择性.