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Organocatalysis in Continuous Flow for Drug Discovery

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Flow Chemistry in Drug Discovery

Part of the book series: Topics in Medicinal Chemistry ((TMC,volume 38))

Abstract

Although organometallic chemistry has been the predominant category for the preferred catalytic transformations applied in pharmaceutical industry since the nineteenth century, during the last 20 years, organocatalytic processes are becoming more common and of wide use in drug discovery field. In particular, enantioselective organocatalysis is emerging as one of the main tools and a greener protocol for the synthesis of chiral molecules. As for today, the main applications of chiral enantiopure compounds are in the pharma and fine chemicals industries, in crop protection, and in the biotechnology area.

Organocatalytic flow processes are of practical application in drug discovery and in the manufacturing of Active Pharmaceutical Ingredients (APIs). In this chapter, we will describe the most recent examples of continuous flow organocatalytic processes reported in the literature for the synthesis of molecules with pharmaceutical interest.

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References

  1. Melchiorre P, Marigo M, Carlone A, Bartoli G (2008) Angew Chem Int Ed 47:6138

    Article  CAS  Google Scholar 

  2. Bertelsen S, Jørgensen KA (2009) Chem Soc Rev 38:2178–2189

    Article  CAS  PubMed  Google Scholar 

  3. Giacalone F, Gruttadauria M, Agrigento P, Noto R (2012) Chem Soc Rev 41:2406–2447

    Article  CAS  PubMed  Google Scholar 

  4. Alemán J, Cabrera S (2013) Chem Soc Rev 42:774–793

    Article  PubMed  Google Scholar 

  5. Jimeno C (2016) Org Biomol Chem 14:6147–6164

    Article  CAS  PubMed  Google Scholar 

  6. Quin Y, Zhu L, Luo S (2017) Chem Rev 117:9433–9520

    Article  Google Scholar 

  7. Chanda T, Zhao JC-G (2018) Adv Synth Catal 360:2–79

    Article  CAS  Google Scholar 

  8. Xiang S, Tan B (2020) Nat Commun 11:3786

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Krištofíková D, Modrocká V, Mečiarová M, Šebesta R (2020) Chem Sus Chem 13:2828–2858

    Article  Google Scholar 

  10. Dalko PI, Moisan L (2004) Angew Chem Int Ed 43:5138–5175

    Article  CAS  Google Scholar 

  11. Tanimu A, Jaenicke S, Alhooshani K (2017) Chem Engineering J 327:792–821

    Article  CAS  Google Scholar 

  12. Colella M, Carlucci C, Luisi R (2018) Top Curr Chem 376:46

    Article  Google Scholar 

  13. de Oliveira PHR, da BM, Santos S, Leão RAC, Miranda LSM, San Gil RAS, de Souza ROMA, Finelli FG (2019) Chem Cat Chem 11:5553–5561

    Google Scholar 

  14. Rodríguez-Escrich C, Pericàs MA (2015) Eur J Org Chem:1173–1188

    Google Scholar 

  15. Atodiresei I, Vila C, Rueping M (2015) ACS Catal 5:1972–1985

    Article  CAS  Google Scholar 

  16. Finelli FG, Miranda LSM, de Souza ROMA (2015) Chem Commun 51:3708–3722

    Article  CAS  Google Scholar 

  17. De Risi C, Bortolini O, Brandolese A, Di Carmine G, Ragno D, Massi A (2020) React Chem Eng 5:1017–1052

    Article  Google Scholar 

  18. Maity C, Trausel F, Eelkema R (2018) Chem Sci 9:5999–6005

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. Burès J, Armstrong A, Blackmond DG (2014) Angew Chem Int Ed 53:8700–8704

    Article  Google Scholar 

  20. Burès J, Armstrong A, Blackmond DG (2013) Pure App Chem 85:1919–1934

    Article  Google Scholar 

  21. Di Marco L, Hans M, Delaude L, Monbaliu J-CM (2016) Chem Eur J 22:4508–4514

    Article  PubMed  Google Scholar 

  22. Zaghi A, Ragno D, Di Carmine G, De Risi C, Bortolini O, Giovannini PP, Fantin G, Massi A (2016) Beilstein J Org Chem 12:2719–2730

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. Ragno D, Brandolese A, Urbani D, Di Carmine G, De Risi C, Bortolini O, Giovannini PP, Massi A (2018) React Chem Eng 3:816–825

    Article  CAS  Google Scholar 

  24. Brandolese A, Ragno D, Di Carmine G, Bernardi T, Bortolini O, Giovannini PP, Ginoble Pandoli O, Altomarec A, Massi A (2019) Org Biomol Chem 16:8955–8964

    Article  Google Scholar 

  25. Abubakar SS, Benaglia M, Rossi S, Annunziata R (2018) Catal Today 308:94–101

    Article  CAS  Google Scholar 

  26. Liu J, Xu J, Li Z, Huang Y, Wang H, Gao Y, Guo T, Ouyang P, Guo K (2017) Eur J Org Chem:3996–4003

    Google Scholar 

  27. Lyons DJM, Crocker RD, Enders D, Nguyen TV (2017) Green Chem 19:3993–3996

    Article  CAS  Google Scholar 

  28. Rattanangkool E, Sukwattanasinitt M, Wacharasindhu S (2017) J Org Chem 82:13256–13262

    Article  CAS  PubMed  Google Scholar 

  29. Schweitzer-Chaput B, Horwitz MA, Beato EP, Melchiorre P (2019) Nat Chem 11:129–135

    Article  CAS  PubMed  Google Scholar 

  30. Vidyacharan S, Ramanjaneyulu BT, Jang S, Kim D-P (2019) ChemSusChem 12:2581–2586

    Article  CAS  PubMed  Google Scholar 

  31. Ranjan P, Ojeda GM, Sharma UK, Van der Eycken EV (2019) Chem Eur J 25:2442–2446

    Article  CAS  PubMed  Google Scholar 

  32. Sagamanova I, Rodríguez-Escrich C, Molnár IG, Sayalero S, Gilmour R, Pericàs MA (2015) ACS Catal 5:6241–6248

    Article  CAS  Google Scholar 

  33. Llanes P, Rodríguez-Escrich C, Sayalero S, Pericàs MA (2016) Org Lett 18:6292–6295

    Article  CAS  PubMed  Google Scholar 

  34. Forni JA, Novaes LFT, Galaverna R, Pastre JC (2018) Catal Today 308:86–93

    Article  CAS  Google Scholar 

  35. Lai J, Sayalero S, Ferrali A, Osorio-Planes L, Bravo F, Rodríguez-Escrich C, Pericàs MA (2018) Adv Synth Catal 360:2914–2924

    Article  CAS  Google Scholar 

  36. Schober L, Ratnam S, Yamashita Y, Adebar N, Pieper M, Berkessel A, Hessel V, Gröger H (2019) Synthesis 51:1178–1184

    Article  CAS  Google Scholar 

  37. Clot-Almenara L, Rodríguez-Escrich C, Osorio-Planes L, Pericàs MA (2016) ACS Catal 6:7647–7651

    Article  CAS  Google Scholar 

  38. Kasaplar P, Ozkal E, Rodríguez-Escrich C, Pericàs MA (2015) Green Chem 17:3122–3129

    Article  CAS  Google Scholar 

  39. Rossi S, Benaglia M, Puglisi A, De Filippo CC, Maggini M (2015) J Flow Chem 5:17–21

    Article  Google Scholar 

  40. Izquierdo J, Pericàs MA (2016) ACS Catal 6:348–356

    Article  CAS  Google Scholar 

  41. Wang S, Izquierdo J, Rodríguez-Escrich C, Pericàs MA (2017) ACS Catal 7:2780–2785

    Article  CAS  Google Scholar 

  42. Izquierdo J, Ayats C, Henseler AH, Pericàs MA (2015) Org Biomol Chem 13:4204–4209

    Article  CAS  PubMed  Google Scholar 

  43. Silvi M, Melchiorre P (2018) Nature 554:41–49

    Article  CAS  PubMed  Google Scholar 

  44. Blakemore DC, Castro L, Churcher I, Rees DC, Thomas AW, Wilson DM, Wood A (2018) Nat Chem 10:383–394

    Article  CAS  PubMed  Google Scholar 

  45. Bogdos MK, Pinard E, Murphy JA, Beilstein J (2018) Org Chem 14:2035–2064

    CAS  Google Scholar 

  46. Sakeda K, Wakabayashi K, Matsushita Y, Ichimura T, Suzuki T, Wada T, Inoue Y (2007) J Photochem Photobiol A 192:166–171

    Article  CAS  Google Scholar 

  47. Neumann M, Zeitler K (2012) Org Lett 14:2658–2661

    Article  CAS  PubMed  Google Scholar 

  48. Tang X-F, Zhao J-N, Wu Y-F, Zheng Z-H, Feng S-H, Yu Z-Y, Liu G-Z, Meng Q-W (2019) Org Biomol Chem 17:7938–7942

    Article  CAS  PubMed  Google Scholar 

  49. Christoffers J, Baro A, Werner T (2004) Adv Synth Catal 346:143–151

    Article  CAS  Google Scholar 

  50. Reddy DS, Shibata N, Nagai J, Nakamura S, Toru T (2009) Angew Chem Int Ed 48:803–806

    Article  Google Scholar 

  51. Fernandes SD, Porta R, Barrulas PC, Puglisi A, Burke AJ, Benaglia M (2016) Molecules 21:1182

    Article  PubMed Central  Google Scholar 

  52. Osorio-Planes L, Rodríguez-Escrich C, Pericàs MA (2016) Cat Sci Technol 6:4686–4689

    Article  CAS  Google Scholar 

  53. Kisszekelyi P, Alammar A, Kupai J, Huszthy P, Barabas J, Holtzl T, Szente L, Bawn C, Adams R, Szekely G (2019) J Catal 371(255):261

    Google Scholar 

  54. Cañellas S, Ayats C, Henseler AH, Pericàs MA (2017) ACS Catal 7:1383–1391

    Article  Google Scholar 

  55. Porta R, Benaglia M, Annunziata R, Puglisi A, Celentano G (2017) Adv Synth Catal 359:2375–2382

    Article  CAS  Google Scholar 

  56. Brenna D, Porta R, Massolo E, Raimondi L, Benaglia M (2017) ChemCatChem 9:941–945

    Article  CAS  Google Scholar 

  57. Ragno D, Carmine GD, Brandolese A, Bortolini O, Giovannini PP, Massi A (2017) ACS Catal 7:6365–6375

    Article  CAS  Google Scholar 

  58. Porta R, Benaglia M, Coccia F, Rossi S, Puglisi A (2015) Symmetry 7:1395–1409

    Article  CAS  Google Scholar 

  59. Ötvös SB, Pericàs MA, Kappe CO (2019) Chem Sci 10:11141–11146

    Article  PubMed  PubMed Central  Google Scholar 

  60. Szcześniak P, Buda S, Lefevre L, Staszewska-Krajewska O, Mlynarski J (2019) Eur J Org Chem:6973–6982

    Google Scholar 

  61. Ötvös SB, Llanes P, Pericàs MA, Kappe CO (2020) Org Lett 22:8122–8126

    Article  PubMed  PubMed Central  Google Scholar 

  62. Morodo R, Gérardy R, Petit G, Monbaliu J-CM (2019) Green Chem 21:4422–4433

    Article  CAS  Google Scholar 

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Author information

Authors and Affiliations

  1. Institute of Chemical Research of Catalonia, ICIQ, Tarragona, Spain

    Laura Amenós, Esther Alza & Miquel A. Pericàs

Authors
  1. Laura Amenós
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  2. Esther Alza
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  3. Miquel A. Pericàs
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Corresponding authors

Correspondence to Esther Alza or Miquel A. Pericàs .

Editor information

Editors and Affiliations

  1. Discovery Chemistry, Janssen Pharmaceutical Companies of J&J, Janssen-Cilag, S.A., Toledo, Spain

    Jesus Alcazar

  2. Faculty of Chemistry, University of Castilla-La Mancha, Ciudad Real, Ciudad Real, Spain

    Antonio de la Hoz

  3. Faculty of Chemistry, University of Castilla-La Mancha, Ciudad Real, Spain

    Angel Díaz-Ortiz

Ethics declarations

Funding: There is no funding related to the chapter.

Ethical Approval: This manuscript is a review of previously published accounts, as such, no animal or human studies were performed.

Informed Consent: No patients were studied in this chapter.

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Amenós, L., Alza, E., Pericàs, M.A. (2021). Organocatalysis in Continuous Flow for Drug Discovery. In: Alcazar, J., de la Hoz, A., Díaz-Ortiz, A. (eds) Flow Chemistry in Drug Discovery. Topics in Medicinal Chemistry, vol 38. Springer, Cham. https://doi.org/10.1007/7355_2021_119

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