Synthesis of Chiral 5-Aryl-2-oxazolidinones via Halohydrin Dehalogenase-Catalyzed Enantio- and Regioselective Ring-Opening of Styrene Oxides

被引：21
|
作者：
Wan, Nanwei [1 ,2 ,3 ]
Zhou, Xiaoying [1 ,2 ,3 ]
Ma, Ran [1 ,2 ,3 ]
Tian, Jiawei [1 ,2 ,3 ]
Wang, Huihui [1 ,2 ,3 ]
Cui, Baodong [1 ,2 ,3 ]
Han, Wenyong [1 ,2 ,3 ]
Chen, Yongzheng [1 ,2 ,3 ]
机构：
[1] Zunyi Med Univ, Sch Pharm, Green Pharmaceut Engn Res Ctr Guizhou Prov, Gener Drug Res Ctr Guizhou Prov,Key Lab Biocataly, Zunyi 563000, Guizhou, Peoples R China
[2] Zunyi Med Univ, Minist Educ, Key Lab Basic Pharmacol, Zunyi, Guizhou, Peoples R China
[3] Zunyi Med Univ, Minist Educ, Joint Int Res Lab Ethnomed, Zunyi, Guizhou, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 05期
基金：
中国国家自然科学基金;
关键词：
Oxazolidinones; Halohydrin dehalogenase; Epoxides; Ring-opening; Cyanate; 5-SUBSTITUTED OXAZOLIDINONES; OXIDATIVE CARBONYLATION; CARBON-DIOXIDE; EFFICIENT; CO2; 2-OXAZOLIDINONES; AZIRIDINES; EPOXIDES; BINDING; POTENT;
D O I：
10.1002/adsc.201901412
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An efficient biocatalytic approach for enantio- and regioselective ring-opening of styrene oxides with cyanate was developed by using the halohydrin dehalogenase HheC from Agrobacterium radiobacter AD1, generating the corresponding chiral 5-aryl-2-oxazolidinones in up to 47% yield and 90% ee. Additionally, the origin of enantioselectivity and regioselectivity of the HheC-catalyzed cyanate-mediated ring-opening process was uncovered by single enantiomer bioconversions and molecular docking study.
引用
收藏
页码：1201 / 1207
页数：7
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共 17 条
  • [1] Enzymatic Kinetic Resolution of Bulky Spiro-Epoxyoxindoles via Halohydrin Dehalogenase-Catalyzed Enantio- and Regioselective Azidolysis
    Zhang, Fang-Rui
    Wan, Nan-Wei
    Ma, Jin-Mei
    Cui, Bao-Dong
    Han, Wen-Yong
    Chen, Yong-Zheng
    [J]. ACS CATALYSIS, 2021, 11 (15) : 9066 - 9072
  • [2] Regioselective Ring-Opening of Styrene Oxide Derivatives Using Halohydrin Dehalogenase for Synthesis of 4-Aryloxazolidinones
    Wan, Nanwei
    Tian, Jiawei
    Zhou, Xiaoying
    Wang, Huihui
    Cui, Baodong
    Han, Wenyong
    Chen, Yongzheng
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (20) : 4651 - 4655
  • [3] Synthesis of Chiral 5-Aryl-2-oxazolidinones via an Ir-BiphPHOX Catalyzed Enantioselective Hydrogenation
    Zhang Tongli
    Yan Jun
    He Jingli
    Kou Xuezhen
    Shen Jiefeng
    Liu Delong
    Zhang Wanbin
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (06) : 1747 - 1758
  • [4] Highly α-position regioselective ring-opening of epoxides catalyzed by halohydrin dehalogenase from Ilumatobacter coccineus: a biocatalytic approach to 2-azido-2-aryl-1-ols
    An, Miao
    Liu, Wanyi
    Zhou, Xiaoying
    Ma, Ran
    Wang, Huihui
    Cui, Baodong
    Han, Wenyong
    Wan, Nanwei
    Chen, Yongzheng
    [J]. RSC ADVANCES, 2019, 9 (29) : 16418 - 16422
  • [5] Facile synthesis of chiral 1,2-chlorohydrins via the ring-opening of meso-epoxides catalyzed by chiral phosphine oxides
    Kotani, Shunsuke
    Furusho, Haruka
    Sugiura, Masaharu
    Nakajima, Makoto
    [J]. TETRAHEDRON, 2013, 69 (14) : 3075 - 3081
  • [6] Ruthenium-catalyzed regioselective synthesis of 2-substituted indoles via ring-opening of epoxides by anilines
    Cho, CS
    Kim, JH
    Choi, HJ
    Kim, TJ
    Shim, SC
    [J]. TETRAHEDRON LETTERS, 2003, 44 (14) : 2975 - 2977
  • [7] Regioselective synthesis of 3,4-diarylpyrimido[1,2-b]indazole derivatives enabled by iron-catalyzed ring-opening of styrene oxides
    Cao, Penghui
    Fan, Guangping
    Zhao, Xiaofei
    Ren, Xinyu
    Wang, Yuru
    Wang, Yuying
    Gao, Qinghe
    [J]. CHEMICAL COMMUNICATIONS, 2024, : 11742 - 11745
  • [8] Synthesis of Planar Chiral 2-Aryl Aroylferrocenes via PalladiumCatalyzed C-C Bond-Cleavage/Ring-Opening Reaction
    Chao, Zengyin
    Li, Na
    Hong, Biqiong
    Ma, Mingming
    Gu, Zhenhua
    [J]. ORGANIC LETTERS, 2021, 23 (20) : 7759 - 7764
  • [9] Highly Regioselective Synthesis of 2,3,5-Trisubstituted Furans via Phosphine-Catalyzed Ring-Opening Cycloisomerization Reactions of Cyclopropenyl Dicarboxylates
    Chen, Jie
    Ni, Shengjun
    Ma, Shengming
    [J]. SYNLETT, 2011, (07) : 931 - 934
  • [10] Rapidly Diverse Synthesis of N-Aryl-5-Substituted-2-Oxazolidinones via Nucleophilic Epoxide Ring Opening and Intramolecular Acyl Substitution of Epoxy Carbamates
    Lin, Nian-Xuan
    Chang, Shih-Ming
    Chiou, Xin-Shun
    Lee, Kelly
    Tsai, Yu-Tung
    Lin, Cheng-Kun
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2024,
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