碱促进脂肪酶催化的阻转异构1,1'-联芳基-2,2'-二醇的动力学拆分
Base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1'-biaryl-2,2'-diols.
作者信息
Moustafa Gamal A I, Kasama Kengo, Higashio Koichi, Akai Shuji
机构信息
Graduate School of Pharmaceutical Sciences, Osaka University 1-6 Yamadaoka Suita, Osaka 565-0871 Japan
Department of Medicinal Chemistry, Faculty of Pharmacy, Minia University Minia 61519 Egypt.
出版信息
RSC Adv. 2019 Jan 9;9(3):1165-1175. doi: 10.1039/c8ra09070j.
Abstract
Herein we report a dramatic acceleration of the lipase-catalyzed kinetic resolution of atropisomeric 1,1'-biaryl-2,2'-diols by the addition of sodium carbonate. This result likely originates from the increased nucleophilicity of the phenolic hydroxyl group toward the acyl-enzyme intermediate. Under these conditions, various substituted -symmetric and non- -symmetric binaphthols and biphenols were efficiently resolved with ∼50% conversion in only 13-30 h with excellent enantioselectivity.
摘要
在此，我们报道了通过添加碳酸钠，脂肪酶催化的阻转异构1,1'-联芳基-2,2'-二醇的动力学拆分显著加速。该结果可能源于酚羟基对酰基酶中间体的亲核性增加。在这些条件下，各种取代的对称和非对称联萘酚和联苯酚仅在13 - 30小时内以约50%的转化率被有效拆分，对映选择性优异。
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