Jamison, T. F. et al.: 2018 Science of Synthesis, 2018/5: Flow Chemistry in Organic Synthesis DOI: 10.1055/sos-SD-228-00214
Flow Chemistry in Organic Synthesis

11 Immobilized Catalysts for Asymmetric Reactions

Weitere Informationen

Buch

Herausgeber: Jamison, T. F.; Koch, G.

Autoren: Beeler, A. B.; Beingessner, R. L.; Bottecchia, C.; Browne, D. L.; Coley, C. W.; Ferguson, S.; Folgueiras-Amador, A. A.; Gilmore, K.; Hicklin, R. W.; Imbrogno, J.; Itsuno, S.; Jamison, T. F.; Jensen, K. F.; Kelly, L. P.; Kerr, M. S.; Kiesman, W. F.; Kim, H.; Kwok, D.-I. A.; Ley, S. V.; Longstreet, A. R.; May, S. A. ; McTeague, T. A.; Mijalis, A. J.; Mo, Y.; Moon, S.; Myerson, A.; Noël, T.; O’Brien, A. G.; O’Brien, M.; O’Mahony, M.; Opalka, S. M.; Pentelute, B. L.; Polyzos, A. ; Schepartz, A.; Seeberger, P. H.; Seo, H.; Steinauer, A.; Stelzer, T.; Stephenson, C. R. J.; Strom, A. E.; Styduhar, E. D.; Sun, A. C.; Telmesani, R.; Thomas, D. A.; Tran, T. H.; Ullah, M. S.; Wicker, A. C.; Wirth, T.; Yoshida, J.

Titel: Flow Chemistry in Organic Synthesis

Print ISBN: 9783132423312; Online ISBN: 9783132423350; Buch-DOI: 10.1055/b-006-161272

Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie

Science of Synthesis Reference Libraries



Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

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

Typ: Mehrbändiges Werk

 


Abstract

Recent applications of polymer-immobilized catalysts for asymmetric reactions are described in this chapter. The chiral catalysts covered include organocatalysts, Lewis acid catalysts, and transition-metal catalysts. Preparation of these chiral polymer-immobilized catalysts and their use in asymmetric reactions are described. The polymer-immobilized catalysts are insoluble in the solvent used for asymmetric reactions and are easily separated from the reaction mixture; the recovered polymeric catalysts can be reused many times without any loss of the catalytic performance. Some of these polymeric catalysts have been used in continuous-flow systems, potentially providing a powerful tool for the synthesis of optically active fine chemicals.

 
  • 1 Atodiresei I, Vila C, Rueping M. ACS Catal 2015; 5: 1972
  • 2 Puglisi A, Benaglia M, Chiroli V. Green Chem 2013; 15: 1790
  • 3 Pastre JC, Brown DL, Ley SV. Chem. Soc. Rev 2013; 42: 8849
  • 4 Tsubogo T, Ishiwata T, Kobayashi S. Angew. Chem. Int. Ed 2013; 52: 6590
  • 5 Cantillo D, Kappe CO. ChemCatChem 2014; 6: 3286
  • 6 Cheng T, Zhao Q, Zhang D, Liu G. Curr. Org. Chem 2015; 19: 667
  • 7 Cinchona Alkaloids in Synthesis and Catalysis: Ligands, Immobilization and Organocatalysis. Song CE. Wiley-VCH; Weinheim, Germany 2009
  • 8 Takata S, Endo Y, Ullah MS, Itsuno S. RSC Adv 2016; 6: 72300
  • 9 Jumde RP, Pietro AD, Manariti A, Mandoli A. Chem.–Asian J 2015; 10: 397
  • 10 Jumde RP, Mandoli A. ACS Catal 2016; 6: 4281
  • 11 Parvez MM, Haraguchi N, Itsuno S. Macromolecules 2014; 47: 1922
  • 12 Itsuno S, Paul DK, Salam MA, Haraguchi N. J. Am. Chem. Soc 2010; 132: 2864
  • 13 Parvez MM, Haraguchi N, Itsuno S. Org. Biomol. Chem 2012; 10: 2870
  • 14 Hassan MM, Haraguchi N, Itsuno S. J. Polym. Sci., Part A: Polym. Chem 2016; 54: 621
  • 15 Porta R, Benaglia M, Coccia F, Cozzi F, Puglisi A. Adv. Synth. Catal 2015; 357: 377
  • 16 Izquierdo J, Ayats C, Henseler AH, Pericàs MA. Org. Biomol. Chem 2015; 13: 4204
  • 17 Suzuki N, Inoue T, Asada T, Akebi R, Kobayashi G, Rikukawa M, Masuyama Y, Ogasawara M, Takahashi T, Thang SH. Chem. Lett 2013; 42: 1493
  • 18 Suzuki N, Akebi R, Inoue T, Rikukawa M, Masuyama Y. Curr. Organocatal 2016; 3: 306
  • 19 Ayats C, Henseler AH, Dibello E, Pericàs MA. ACS Catal 2014; 4: 3027
  • 20 Deng J, Zhao B, Deng J. Ind. Eng. Chem. Res 2016; 55: 7328
  • 21 Colby Davie EA, Mennen SM, Xu Y, Miller SJ. Chem. Rev 2007; 107: 5759
  • 22 Revell JD, Wennemers H. Curr. Opin. Chem. Biol 2007; 11: 269
  • 23 Itsuno S, Sakakura M, Ito K. J. Org. Chem 1990; 55: 6047
  • 24 Arakawa Y, Wiesner M, Wennemers H. Adv. Synth. Catal 2011; 353: 1201
  • 25 Arakawa Y, Wennemers H. ChemSusChem 2013; 6: 242
  • 26 Wang Y, Shen H, Zhou L, Hu F, Xie S, Jiang L. Catal. Sci. Technol 2016; 2: 6739
  • 27 Akagawa K, Suzuki R, Kudo K. Asian J. Org. Chem 2014; 3: 514
  • 28 Akagawa K, Takigawa S, Nagamine IS, Umezawa R, Kudo K. Org. Lett 2013; 15: 4964
  • 29 Akagawa K, Suzuki R, Kudo K. Adv. Synth. Catal 2012; 354: 1280
  • 30 Fields GB, Noble RL. Int. J. Pept. Protein Res 1990; 35: 161
  • 31 Ahrendt KA, Borths CJ, MacMillan DWC. J. Am. Chem. Soc 2000; 122: 4243
  • 32 Jen WS, Wiener JJM, MacMillan DWC. J. Am. Chem. Soc 2000; 122: 9874
  • 33 Paras NA, MacMillan DWC. J. Am. Chem. Soc 2001; 123: 4370
  • 34 Brochu MP, Brown SP, MacMillan DWC. J. Am. Chem. Soc 2004; 126: 4108
  • 35 Beeson TD, MacMillan DWC. J. Am. Chem. Soc 2005; 127: 8826
  • 36 Hechavarria Fonseca MT, List B. Angew. Chem. Int. Ed 2004; 43: 3958
  • 37 Itsuno S, Onami T, Takenaka N, Haraguchi N. Adv. Synth. Catal 2015; 357: 3995
  • 38 Haraguchi N, Kiyono H, Takemura Y, Itsuno S. Chem. Commun. (Cambridge) 2012; 48: 4011
  • 39 Haraguchi N, Takemura Y, Itsuno S. Tetrahedron Lett 2010; 51: 1205
  • 40 Ranjbar S, Riente P, Rodríguez-Escrich C, Yadav J, Raminene K, Pericàs MA. Org. Lett 2016; 18: 1602
  • 41 Llanes P, Rodríguez-Escrich C, Sayalero S, Pericàs MA. Org. Lett 2016; 18: 6292
  • 42 Sagamanova I, Rodríguez-Escrich C, Molnár IG, Sayalero S, Gilmour R, Pericàs MA. ACS Catal 2015; 5: 6241
  • 43 Cañellas S, Ayats C, Henseler AH, Pericàs MA. ACS Catal 2017; 7: 1383
  • 44 Clot-Almenara L, Rodríguez-Escrich C, Osorio-Planes L, Pericàs MA. ACS Catal 2016; 6: 7647
  • 45 Osorio-Planes L, Rodríguez-Escrich C, Pericàs MA. Chem.–Eur. J 2014; 20: 2367
  • 46 Izquierdo J, Pericàs MA. ACS Catal 2016; 6: 348
  • 47 Wang S, Izquierdo J, Rodríguez-Escrich C, Pericàs MA. ACS Catal 2017; 7: 2780
  • 48 Tsubogo T, Yamashita Y, Kobayashi S. Angew. Chem. Int. Ed 2009; 48: 9117
  • 49 Ishitani H, Saito Y, Tsubogo T, Kobayashi S. Org. Lett 2016; 18: 1346
  • 50 Yadhav J, Stanton GR, Fan X, Robinson JR, Schelter EJ, Walsh PJ, Pericàs MA. Chem.–Eur. J 2014; 20: 7122
  • 51 Sugie H, Hashimoto Y, Haraguchi N, Itsuno S. J. Organomet. Chem 2014; 751: 711
  • 52 Itsuno S, Hashimoto Y, Haraguchi N. J. Polym. Sci., Part A: Polym. Chem 2014; 52: 3037
  • 53 Shan W, Meng F, Wu Y, Mao F, Li X. J. Organomet. Chem 2011; 696: 1687
  • 54 Wei J, Zhang X, Zhang X, Zhao Y, Li R, Yang Q. ChemCatChem 2014; 6: 1368
  • 55 Itsuno S, Takahashi S. ChemCatChem 2017; 9: 385
  • 56 Hannedouche J, Clarkson GL, Wills M. J. Am. Chem. Soc 2004; 126: 986
  • 57 Matharu DS, Morris DJ, Clarkson GL, Wills M. Chem. Commun. (Cambridge) 2006; 3232
  • 58 Dimroth J, Keilitz J, Schedler U, Schomacker R, Haag R. Adv. Synth. Catal 2010; 352: 5497
  • 59 Dimroth J, Schedler U, Keilitz J, Haag R, Schomacker R. Adv. Synth. Catal 2011; 353: 1355
  • 60 Chen M, Zhang Z, Yu Z, Qiu H, Ma B, Wu H. ACS Catal 2015; 5: 7488