Abstract: Chiral compounds have already presented unique advantages in many fields, such as medicine field, material field, etc. In face of the increasingly requirements for optical pure compounds, many methods have been developed. Among them, catalytic cycle involving chemical enzyme and multienzyme attracted more and more attention due to the advantages of environment-friendly process, high selectivity, and mild conditions. In this paper, the latest development of the cyclic network for the synthesis of optically pure compounds is reviewed, including three methods. (1) Dynamic kinetic resolution (DKR): most of the research work focused on the resolution of secondary alcohols, especially aromatic secondary alcohols. However, chiral resolution of anines is still challenging problems. (2) Minor enantiomer recycling (MER): it is a new reaction mode in the field of chiral synthesis and has been successfully applied to the synthesis of chiral cyanohydrin esters and cyclic chiral amines. (3) Cyclic deracemisation (CyD): this is an attractive method for the synthesis of chiral amines.
作者简介: 张媛媛,河北工业大学化工学院硕士研究生。2017年于邢台学院应用化学专业本科毕业,2020年于河北工业大学化工学院有机化学专业硕士毕业。主要从事不对称催化合成研究。温叶倩,河北工业大学化工学院副教授,硕士研究生导师。2005年于河北工业大学应用化学专业本科毕业,2011年于大连理工大学精细化工国家重点实验室应用化学专业博士毕业,2012和2013年在瑞典皇家工学院有机化学专业从事博士后。目前从事不对称催化合成、高分子材料合成、生物质利用等方面的研究工作,在Catalysis Science & Technology、Applied Catalysis A, General、the Journal of Organic Chemistry、Diamond & Related Materials等期刊上发表多篇论文。
引用本文:
张媛媛, 温叶倩. 生物酶与化学催化剂结合在合成手性化合物中的应用[J]. 材料导报, 2022, 36(2): 20040218-10.
ZHANG Yuanyuan, WEN Yeqian. Application of Biological Enzyme and Chemical Catalyst in Synthesis of Chiral Compounds. Materials Reports, 2022, 36(2): 20040218-10.
1 Zhai F, Feng Y, Zhou K, et al. Journal of Materials Chemistry C, 2019, 7, 2146. 2 Zhuang T T, Li Y, Gao X, et al. Nature Nanotechnology, 2020, 15, 192. 3 De Miranda A S, Miranda L S M, De Souza R O M A. Biotechnology Advances, 2015, 33(5), 372. 4 Yang Y, Zhang J, Wu D, et al. Biotechnology Advances, 2014, 32(3), 642. 5 Lee J H, Han K, Kim M J, et al. European Journal of Organic Chemistry, 2010, 2010(6), 999. 6 Dinh P M, Howarth J A, Hudnott A R, et al. Tetrahedron Letters, 1996, 37(42), 7623. 7 Larsson A L E, Persson B A, Bäckvall J E. Angewandte Chemie International Edition in English, 1997, 36(11), 1211. 8 Lee J H, Kim N, Kim M J, et al. ChemCatChem, 2011, 3(2), 354. 9 Mavrynsky D, Päiviö M, Lundell K, et al. European Journal of Organic Chemistry, 2010, 2009(9), 1317. 10 Fernández-Salas J A, Manzini S, Nolan S P. Chemistry-A European Journal, 2014, 20(41), 13132. 11 Do Y, Hwang I C, Kim M J, et al. The Journal of Organic Chemistry, 2010, 75(16), 5740. 12 Päiviö M, Mavrynsky D, Leino R, et al. European Journal of Organic Chemistry, 2011, 2011(8), 1452. 13 Merabet-Khelassi M, Vriamont N, Aribi-Zouioueche L, et al. Tetrahedron: Asymmetry, 2011, 22(18-19), 1790. 14 Sato Y, Kayaki Y, Ikariya T. Chemical Communications, 2012, 48(30), 3635. 15 Dinh P M, Howarth J A, Hudnott A R, et al. Tetrahedron Letters, 1996, 37(42), 7623. 16 El-Sepelgy O, Alandini N, Rueping M. Angewandte Chemie International Edition, 2016, 55(43), 13602. 17 El-Sepelgy O, Brzozowska A, Rueping M. ChemSusChem, 2017, 10(8), 1664. 18 Berkessel A, Sebastian-Ibarz M L, Müller T N. Angewandte Chemie International Edition, 2006, 45(39), 6567. 19 Wuyts S, Wahlen J, Jacobs P A, et al. Green Chemistry, 2007, 9(10), 1104. 20 Akai S, Tanimoto K, Kanao Y, et al. Angewandte Chemie International Edition, 2006, 45(16), 2592. 21 Akai S, Hanada R, Fujiwara N, et al. Organic Letters, 2010, 12(21), 4900. 22 Egi M, Sugiyama K, Saneto M, et al. Angewandte Chemie International Edition, 2013, 52(13), 3654. 23 Sugiyama K, Oki Y, Kawanishi S, et al. Catalysis Science & Technology, 2016, 6(13), 5023. 24 Cao H, Zhu X H, Wang D, et al. ACS Catalysis, 2015, 5(1), 27. 25 El-Sepelgy O, Alandini N, Rueping M. Angewandte Chemie International Edition, 2016, 128, 13800. 26 Rawlings A J, Diorazio L J, Wills M. Organic Letters, 2015, 17(5), 1086. 27 Yan T, Feringa B L, Barta K. ACS Catalysis, 2015, 6(1), 381. 28 Trieu-Tien T, Delphine S M, Albert P, et al. Chemistry, 2015, 46(37), 7066. 29 Gustafson K P J, Guemundsson A, Lewis K, et al. Chemistry-A European Journal, 2017, 23(5), 1048. 30 Yang Q, Zhang N, Liu M, et al. Tetrahedron Letters, 2017, 58(25), 2487. 31 Yun I, Park J Y, Park J, et al. The Journal of Organic Chemistry, 2019, 84(24), 16293. 32 Hilker I, Rabani G, Verzijl G K M, et al. Angewandte Chemie International Edition, 2006, 45(13), 2130. 33 Zhang Y, Zhu Q, Fei Z, et al. European Polymer Journal, 2019, 119, 52. 34 Yang Q, Zhao F, Zhang N, et al. Chemical Communications, 2018, 54(100), 14065. 35 Murahashi S, Yoshimura N, Tsumiyama T, et al. Journal of the American Chemical Society, 1983, 105(15), 5002. 36 Reetz M T, Schimossek K. CHIMIA International Journal for Chemistry, 1996, 50(12), 668. 37 Engström K, Johnston E V, Verho O, et al. Angewandte Chemie International Edition, 2013, 52(52), 14006. 38 Filice M, Marciello M, del Puerto Morales M, et al. Chemical Communications, 2013, 49(61), 6876. 39 Xu Y, Wang M, Feng B, et al. Catalysis Science & Technology, 2017, 7(24), 5838. 40 Gao S, Wang Z, Ma L, et al. ACS Catalysis, 2020, 10 (2), 1375. 41 Li X, Cao Y, Luo K, et al. Nature Catalysis, 2019, 2(8), 718. 42 Strauss U T, Faber K. Tetrahedron: Asymmetry, 1999, 10(21), 4079. 43 Asukawa K, Hasemi R, Asano Y. Advanced Synthesis & Catalysis, 2011, 353(13), 2328. 44 Musa M M, Patel J M, Nealon C M, et al. Journal of Molecular Catalysis B: Enzymatic, 2015, 115, 155. 45 Karume I, Musa M M, Bsharat O, et al. RSC advances, 2016, 6(99), 96616. 46 Popnoński J, Reiter T, Kroutil W. ChemCatChem, 2018, 10(4), 763. 47 Musa M M, Hollmann F, Mutti F G. Catalysis Science & Technology, 2019, 9(20), 5487. 48 Wingstrand E, Laurell A, Fransson L, et al. Chemistry-A European Journal, 2009, 15(44), 12107. 49 Moberg C. Accounts of Chemical Research, 2016, 49(12), 2736. 50 Moberg C. Pure and Applied Chemistry, 2016, 88(4), 309. 51 Lundgren S, Wingstrand E, Penhoat M, et al. Journal of the American Chemical Society, 2005, 127(33), 11592. 52 Hamberg A, Lundgren S, Penhoat M, et al. Journal of the American Chemical Society, 2006, 128(7), 2234. 53 Laurell A, Moberg C. European Journal of Organic Chemistry, 2011, 2011(20-21), 3980. 54 Wen Y Q, Hertzberg R, Gonzalez I, et al. Chemistry, 2014, 20(13), 3806. 55 Hertzberg R, Moberg C. The Journal of Organic Chemistry, 2013, 78(18), 9174. 56 Hertzberg R, Dinér P, Moberg C. Synthesis, 2016, 48(19), 3175. 57 Hertzberg R, Monreal S G, Moberg C. The Journal of Organic Chemistry, 2015, 80(5), 2937. 58 Guo X, Okamoto Y, Schreier M R, et al. Chemical Science, 2018, 9(22), 5052. 59 Aranda C, Oksdath-Mansilla G, Bisogno F, et al. Advanced Synthesis & Catalysis. 2020, 362 (6), 1233. 60 Schmermund L, Jurkaš V, Özgen F F, et al. CS Catalysis, 2019, 9(5), 4115. 61 Rudroff F, Mihovilovic M D, Gröger H, et al. Nature Catalysis, 2018, 1(1), 12. 62 Wen Y Q, Hertzberg R, Moberg C E. The Journal of Organic Chemistry, 2014, 79(13), 6172. 63 Seel C J, Gulder T. ChemBioChem, 2019, 20(15), 1871. 64 Gong R, Yao P, Chen X, et al. ChemCatChem, 2018, 10(2), 387. 65 Yao P, Cong P, Gong R, et al. ACS Catalysis, 2018, 8(3), 1648. 66 Cosgrove S C, Hussain S, Turner N J, et al. ACS Catalysis, 2018, 8(6), 5570. 67 Aleku G A, Mangas-Sanchez J, Citoler J, et al. ChemCatChem, 2018, 10(3), 515. 68 Nosek V, Míšek J. Angewandte Chemie International Edition, 2018, 57(31), 9849.