Base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1 '-biaryl-2,2 '-diols

Moustafa Gamal A. I.; Kasama Kengo; Higashio Koichi; Akai Shuji

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Base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1 '-biaryl-2,2 '-diols

机译：基础促进的脂肪酶催化的阿累物体1,1'-α-2,2'-二醇的动力学分辨率

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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 C-2-symmetric and non-C-2-symmetric binaphthols and biphenols were efficiently resolved with similar to 50% conversion in only 13-30 h with excellent enantioselectivity.

机译：在此，通过加入碳酸钠报告了阿里多基1,1'----1'-2,2,2'-二醇的脂肪酶催化动力学分辨率的显着加速。该结果可能源于酚羟基的增加的酚羟基朝向酰基酶中间体的亲核性。在这些条件下，有效地解决了各种取代的C-2 - 对称和非C-2-对称胆碱和联苯酚，其仅在仅13-30小时内具有相似的50％转化，具有优异的对映选择性。

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《RSC Advances》 |2019年第3期|共11页
作者
Moustafa Gamal A. I.; Kasama Kengo; Higashio Koichi; Akai Shuji;
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Osaka Univ Grad Sch Pharmaceut Sci 1-6 Yamadaoka Suita Osaka 5650871 Japan;

Osaka Univ Grad Sch Pharmaceut Sci 1-6 Yamadaoka Suita Osaka 5650871 Japan;

Osaka Univ Grad Sch Pharmaceut Sci 1-6 Yamadaoka Suita Osaka 5650871 Japan;

Osaka Univ Grad Sch Pharmaceut Sci 1-6 Yamadaoka Suita Osaka 5650871 Japan;

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正文语种 eng
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1. Base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1 '-biaryl-2,2 '-diols [J] . Moustafa Gamal A. I., Kasama Kengo, Higashio Koichi, RSC Advances . 2019,第3期

机译：基础促进的脂肪酶催化的阿累物体1,1'-α-2,2'-二醇的动力学分辨率
2. Lipase-Catalyzed Dynamic Kinetic Resolution of C-1- and C-2-Symmetric Racemic Axially Chiral 2,2 '-Dihydroxy-1,1 '-biaryls [J] . Moustafa Gamal A. I., Oki Yasuhiro, Akai Shuji Angewandte Chemie . 2018,第32期

机译：脂肪酶催化的C-1和C-2 - 对称外消旋轴向手性2,2'-DiHydroxy-1,1'架的动态动力学分辨率
3. Kinetic Resolution of 1,1'-Biaryl-2,2'-Diols and Amino Alcohols through NHC-Catalyzed Atroposelective Acylation [J] . Shenci Lu, Si Bei Poh, Yu Zhao Angewandte Chemie . 2014,第41期

机译：NHC催化的Atroposelective酰化反应的1,1'-Biaryl-2,2'-二醇和氨基醇的动力学拆分
4. Synthesis of 2,2-dinitroethene-1,1-diamine from 2-methylpyrimidine-4,6-diol and treatment of the dinitromethane produced [C] . Zdenek Jalovy, Milan Jancik, Jindrich Masin, Seminar on new trends in research of energetic materials . 2018

机译：由2-甲基嘧啶-4,6-二醇合成2,2-二硝基乙烯-1,1-二胺及处理生成的二硝基甲烷
5. Synthesis of 1,1'-binapthalene-2,2'-diol sulfide with the determination and measurement of its biological activity. [D] . Robinson, Kevin D. 2007

机译：测定和测量其生物活性的1,1'-联萘-2,2'-二醇硫化物的合成。
6. 1,1′-Dibenzyl-5,5′′-dichloro-1,1′′,2,2′′-tetrahydrodispiro[indole-3,7′-[6,9]diazatricyclo[7.3.0.02,6]dodecane-8′,3′′-indole]-2,2′′-dione [O] . Khalil Al Mamari, Hamid Ennajih, Rachid Bouhfid, 2015

机译：1,1'-二苄基-5,5'-二氯-1,1''，2,2''-四氢二螺[吲哚-3,7'-[6,9]二氮杂三环[7.3.0.02,6]十二烷-8′，3′′-吲哚] -2,2′′-二酮
7. Innenrücktitelbild: Lipase-Catalyzed Dynamic Kinetic Resolution of C 1 - and C 2 -Symmetric Racemic Axially Chiral 2,2′-Dihydroxy-1,1′-biaryls (Angew. Chem. 32/2018) [O] . Gamal A. I. Moustafa, Yasuhiro Oki, Shuji Akai 2018

机译：Innenrücktitelbild：脂肪酶催化的C 1 - 和C 2-二羟基外消旋的动态动态动力分辨率轴向手性2,2'-二氢XY-1,1'-纤维素（Angew。Chem.20018）
8. Syntes och Uppskaining av 2,2-Dinitro-Eten-1,1-Diamin (The Synthesis and Scaling up of 2,2-Dinitro-Ethene-1,1 Diamine). [R] . Johansson, M. 1999

机译：使用2,2-二硝基-Eten-1,1-二胺（2,2-二硝基 - 乙烯-1,1二胺的合成和结垢）进行合成。

Base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1 '-biaryl-2,2 '-diols

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