Download PDF
Ackermann, L. : 2022 Science of Synthesis, 2021/5: Electrochemistry in Organic Synthesis DOI: 10.1055/sos-SD-236-00237
Electrochemistry in Organic Synthesis

12 Asymmetric Electrosynthesis

More Information

Book

Editor: Ackermann, L. 

Authors: Ackermann, L. ; Brown, R. C. D. ; Enders, P.; Fang, P.; Folgueiras-Amador, A. A. ; Francke, R. ; Galczynski, J.; Gosmini, C. ; Hodgson, J. W.; Hou, Z.-W.; Huang, H.; Huang, Z.; Inagi, S. ; Kuciński, K. ; Kuriyama, M. ; Lam, K. ; Lambert, T. H.; Leech, M. C. ; Lennox, A. J. J. ; Lin, Z.; Little, R. D.; Massignan, L.; Mei, T.-S.; Meyer, T. H.; Moeller, K. D. ; Onomura, O. ; Prudlik, A.; Ruan, Z. ; Scheremetjew, A. ; Schiltz, P.; Selt, M.; Villani, E. ; Waldvogel, S. R. ; Wang, Z.-H.; Wu, T.; Xing, Y.-K.; Xu, H.-C. ; Yamamoto, K. 

Title: Electrochemistry in Organic Synthesis

Print ISBN: 9783132442122; Online ISBN: 9783132442146; Book DOI: 10.1055/b000000126

1st edition © 2022. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

Also available at
 


Abstract

The merging of asymmetric synthesis and electrochemistry offers powerful and environ-mentally benign protocols for the synthesis of optically active compounds. As electro-chemical reactions are performed under unique conditions compared with conventional chemical reactions, a variety of chiral sources have been investigated to achieve efficient asymmetric induction. In this review, selected examples of enantioselective electrosyn-thesis by using chiral mediators, organocatalysts, metal catalysts, and modified electrodes under both electrooxidative and electroreductive conditions are described. These reactions are organized according to the type of chiral source employed. Asymmetric electrosynthesis via memory of chirality is also included.

Key words

asymmetric synthesis - electrosynthesis - anodic oxidation - cathodic reduction - mediators - organocatalysts - metal catalysts - memory of chirality - modified electrodes - N-oxyls - radical coupling - oxidative coupling - reductive coupling - difunctionalization of alkenes - kinetic resolution - amines - hypervalent iodine - cobalt - nickel - copper - rhodium - palladium
 
  • 1 Gourley RN, Grimshaw J, Miller PG. Chem. Commun. 1967; 1278
  • 2 Kopilov J, Kariv E, Miller LL. J. Am. Chem. Soc. 1977; 99: 3450
  • 3 Schoo N, Schäfer H.-J. Liebigs Ann. Chem. 1993; 601
  • 4 Chen B.-L, Tu Z.-Y, Zhu H.-W, Sun W.-W, Wang H, Lu J.-X. Electrochim. Acta 2014; 116: 475
  • 5 Watkins BF, Behling JR, Kariv E, Miller LL. J. Am. Chem. Soc. 1975; 97: 3549
  • 6 Firth BE, Miller LL. J. Am. Chem. Soc. 1976; 98: 8272
  • 7 Seebach D, Oei H.-A, Daum H. Chem. Ber. 1977; 110: 2316
  • 8 Lin Q, Li L, Luo S. Chem.–Eur. J. 2019; 25: 10033
    PubMed
  • 9 Ghosh M, Shinde VS, Rueping M. Beilstein J. Org. Chem. 2019; 15: 2710
    PubMed
  • 10 Chang X, Zhang Q, Guo C. Angew. Chem. Int. Ed. 2020; 59: 12612
    PubMed
  • 11 Horner L, Degner D. Electrochim. Acta 1974; 19: 611
  • 12 Kodama Y, Fujiwara A, Kawamoto H, Ohta N, Kitani A, Ito S. Chem. Lett. 2001; 30: 240
  • 13 Yadav AK, Singh A. Bull. Chem. Soc. Jpn. 2002; 75: 587
  • 14 Maekawa H, Itoh K, Goda S, Nishiguchi I. Chirality 2003; 15: 95
    PubMed
  • 15 Schmitz LM, Rosenthal K, Lütz S, In: Bioelectrosynthesis. Advances in Biochemical Engineering/Biotechnology Harnisch F, Holtmann D. Springer Cham, Switzerland 2017; 167. 87
  • 16 Yan M, Kawamata Y, Baran PS. Chem. Rev. 2017; 117: 13230
    PubMed
  • 17 Nutting JE, Rafiee M, Stahl SS. Chem. Rev. 2018; 118: 4834
    PubMed
  • 18 Kashiwagi Y, Kurashima F, Kikuchi C, Anzai J.-i, Osa T, Bobbitt JM. Tetrahedron Lett. 1999; 40: 6469
  • 19 Kuroboshi M, Yoshihisa H, Cortona MN, Kawakami Y, Gao Z, Tanaka H. Tetrahedron Lett. 2000; 41: 8131
  • 20 Shiigi H, Mori H, Tanaka T, Demizu Y, Onomura O. Tetrahedron Lett. 2008; 49: 5247
  • 21 Elsherbini M, Wirth T. Chem.–Eur. J. 2018; 24: 13399
    PubMed
  • 22 Gao W.-C, Xiong Z.-Y, Pirhaghani S, Wirth T. Synthesis 2019; 51: 276
  • 23 Yoshida J.-i, Nagaki A, In: Microreactors in Preparative Chemistry Reschetilowski W. Wiley-VCH Weinheim, Germany 2013; 231
    Crossref
  • 24 Folgueiras-Amador AA, Wirth T. Science of Synthesis: Flow Chemistry in Organic Synthesis. 2018: 147
    Google Scholar
  • 25 Girard SA, Knauber T, Li C.-J. Angew. Chem. Int. Ed. 2014; 53: 74
    PubMed
  • 26 Fu N, Li L, Yang Q, Luo S. Org. Lett. 2017; 19: 2122
    PubMed
  • 27 Gao P.-S, Weng X.-J, Wang Z.-H, Zheng C, Sun B, Chen Z.-H, You S.-L, Mei T.-S. Angew. Chem. Int. Ed. 2020; 59: 15254
    PubMed
  • 28 Li L, Li Y, Fu N, Zhang L, Luo S. Angew. Chem. Int. Ed. 2020; 59: 14347
    PubMed
  • 29 Campbell CD, Rees CW. J. Chem. Soc. C 1969; 5: 742
  • 30 Jensen KL, Franke PT, Nielsen LT, Daasbjerg K, Jørgensen KA. Angew. Chem. Int. Ed. 2010; 49: 129
    PubMed
  • 31 Ho X.-H, Mho S.-i, Kang H, Jang H.-Y. Eur. J. Org. Chem. 2010; 4436
  • 32 Lu F.-Y, Chen Y.-J, Chen Y, Ding X, Guan Z, He Y.-H. Chem. Commun. (Cambridge) 2020; 56: 623
    PubMed
  • 33 Chang X, Zhang J, Zhang Q, Guo C. Angew. Chem. Int. Ed. 2020; 59: 18500
    PubMed
  • 34 Day DP, Sellars PB. Eur. J. Org. Chem. 2017; 1034
  • 35 Bulman Page PC, Marken F, Williamson C, Chan Y, Buckley BR, Bethell D. Adv. Synth. Catal. 2008; 350: 1149
  • 36 Kolb HC, VanNieuwenhze MS, Sharpless KB. Chem. Rev. 1994; 94: 2483
  • 37 Amundsen AR, Balko EN. J. Appl. Electrochem. 1992; 22: 810
  • 38 Torii S, Liu P, Bhuvaneswari N, Amatore C, Jutand A. J. Org. Chem. 1996; 61: 3055
    PubMed
  • 39 Minato D, Arimoto H, Nagasue Y, Demizu Y, Onomura O. Tetrahedron 2008; 64: 6675
  • 40 Zhang L, Meggers E. Chem.–Asian J. 2017; 12: 2335
    PubMed
  • 41 Huang X, Zhang Q, Lin J, Harms K, Meggers E. Nat. Catal. 2019; 2: 34
  • 42 Yan M, Kawamata Y, Baran PS. Angew. Chem. Int. Ed. 2018; 57: 4149
    PubMed
  • 43 Zhang Q, Chang X, Peng L, Guo C. Angew. Chem. Int. Ed. 2019; 58: 6999
    PubMed
  • 44 Liao G, Zhou T, Yao Q.-J, Shi B.-F. Chem. Commun. (Cambridge) 2019; 55: 8514
    PubMed
  • 45 Dhawa U, Tian C, Wdowik T, Oliveira JCA, Hao J, Ackermann L. Angew. Chem. Int. Ed. 2020; 59: 13451
    PubMed
  • 46 Fu N, Song L, Liu J, Shen Y, Siu JC, Lin S. J. Am. Chem. Soc. 2019; 141: 14480
    PubMed
  • 47 Song L, Fu N, Ernst BG, Lee WH, Frederick MO, DiStasio Jr RA, Lin S. Nat. Chem. 2020; 12: 747
    PubMed
  • 48 Qiu H, Shuai B, Wang Y.-Z, Liu D, Chen Y.-G, Gao P.-S, Ma H.-X, Chen S, Mei T.-S. J. Am. Chem. Soc. 2020; 142: 9872
    PubMed
  • 49 Akiyama T. Chem. Rev. 2007; 107: 5744
    PubMed
  • 50 Terada M. Synthesis 2010; 1929
  • 51 Brunel JM. Chem. Rev. 2007; 107: PR1
  • 52 Durandetti M, Gosmini C, Périchon J. Tetrahedron 2007; 63: 1146
  • 53 Weix DJ. Acc. Chem. Res. 2015; 48: 1767
    PubMed
  • 54 Poremba KE, Dibrell SE, Reisman SE. ACS Catal. 2020; 10: 8237
    PubMed
  • 55 DeLano TJ, Reisman SE. ACS Catal. 2019; 9: 6751
    PubMed
  • 56 Cherney AH, Reisman SE. J. Am. Chem. Soc. 2014; 136: 14365
    PubMed
  • 57 Fuchigami T, Inagi S, In: Organic Electrochemistry Hammerich O, Speiser B. CRC Boca Raton, FL 2016; 1489
  • 58 Arnaboldi S, Magni M, Mussini PR. Curr. Opin. Electrochem. 2018; 8: 60
  • 59 Komori T, Nonaka T. J. Am. Chem. Soc. 1984; 106: 2656
  • 60 Kawabata S, Iwata N, Yoneyama H. Chem. Lett. 2000; 29: 110
  • 61 Yamagishi A, Aramata A. J. Chem. Soc., Chem. Commun. 1984; 452
  • 62 Kashiwagi Y, Kurashima F, Chiba S, Anzai J.-i, Osa T, Bobbitt JM. Chem. Commun. (Cambridge) 2003; 114
    PubMed
  • 63 Osa T, Kashiwagi Y, Yanagisawa Y, Bobbitt JM. J. Chem. Soc., Chem. Commun. 1994; 2535
  • 64 Kashiwagi Y, Yanagisawa Y, Kurashima F, Anzai J.-i, Osa T, Bobbitt JM. Chem. Commun. (Cambridge) 1996; 2745
  • 65 Yanagisawa Y, Kashiwagi Y, Kurashima F, Anzai J.-i, Osa T, Bobbitt JM. Chem. Lett. 1996; 1043
  • 66 Yang H.-P, Fen Q, Wang H, Lu J.-X. Electrochem. Commun. 2016; 71: 38
  • 67 Yutthalekha T, Wattanakit C, Lapeyre V, Nokbin S, Warakulwit C, Limtrakul J, Kuhn A. Nat. Commun. 2016; 7: 12678
    PubMed
  • 68 Kashiwagi Y, Ono H, Osa T. Chem. Lett. 1993; 81
  • 69 Kawabata T, Fuji K, In: Topics in Stereochemistry Denmark SE. John Wiley & Sons New York 2003; 23. 175
  • 70 Matsumura Y, Shirakawa Y, Satoh Y, Umino M, Tanaka T, Maki T, Onomura O. Org. Lett. 2000; 2: 1689
    PubMed
  • 71 Wanyoike GN, Onomura O, Maki T, Matsumura Y. Org. Lett. 2002; 4: 1875
    PubMed
  • 72 Wanyoike GN, Matsumura Y, Kuriyama M, Onomura O. Heterocycles 2010; 80: 1177