Skip to main content

Chiral Metal Nanoparticles for Asymmetric Catalysis

  • Chapter
  • First Online:
Nanoparticles in Catalysis

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 66))

Abstract

Metal nanoparticles modified by chiral ligands or chiral polymers, called as “chiral metal nanoparticles,” are promising catalysts for asymmetric organic transformations. In this chapter, the class of chiral modifiers is focused to overview advance in the field of metal nanoparticle-catalyzed asymmetric reactions.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 259.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Ojima I (2010) Catalytic asymmetric synthesis. Wiley, Hoboken

    Book  Google Scholar 

  2. Christmann M, Bräse S (2012) Asymmetric synthesis II: more methods and applications. Wiley, Hoboken

    Book  Google Scholar 

  3. Akabori S, Sakurai S, Izumi Y, Fujii Y (1956) Nature 178:323

    Article  CAS  Google Scholar 

  4. Izumi Y, Imaida M, Fukawa H, Akabori S (1963) Bull Chem Soc Jpn 36:21

    Article  Google Scholar 

  5. Izumi Y, Imaida M, Fukawa H, Akabori S (1963) Bull Chem Soc Jpn 36:155

    Article  CAS  Google Scholar 

  6. Tatsumi S, Imaida M, Fukuda Y, Izumi Y, Akabori S (1964) Bull Chem Soc Jpn 37:846

    Article  CAS  Google Scholar 

  7. Orito Y, Imai S, Niwa S (1979) Nippon Kagaku Kaishi:1118

    Google Scholar 

  8. Orito Y, Imai S, Niwa S, Nguyen GH (1979) J Synth Org Chem Jpn 37:173

    Article  CAS  Google Scholar 

  9. Rodríguez-García L, Hungerbühler K, Baiker A, Meemken F (2017) ACS Catal 7:3799

    Article  CAS  Google Scholar 

  10. Xue XR, Wang YH, Han FS (2017) Chem Commun 53:3346

    Article  CAS  Google Scholar 

  11. Yang T, Lou LL, Yu WJ, Feng YJ, Li H, Yu K, Liu SX (2017) ChemCatChem 9:458

    Article  CAS  Google Scholar 

  12. Mao C, Zhang J, Xiao MT, Liu YJ, Zhang XQ (2018) Curr Appl Phys 18:1480

    Article  Google Scholar 

  13. Meemken F, Rodriguez-Garcia L (2018) J Phys Chem Lett 9:996

    Article  CAS  PubMed  Google Scholar 

  14. Xue XR, Chen P, Xu P, Wang YH (2018) Catal Commun 110:55

    Article  CAS  Google Scholar 

  15. Xue XR, Zhao ZH, Wang YH (2018) Org Chem Front 5:3585

    Article  CAS  Google Scholar 

  16. Blaser H-U, Studer M (2007) Acc Chem Res 40:1348

    Article  CAS  PubMed  Google Scholar 

  17. Zhan E, Chen C, Li Y, Shen W (2015) Cat Sci Technol 5:650

    Article  CAS  Google Scholar 

  18. Baiker A (2015) Chem Soc Rev 44:7449

    Article  CAS  PubMed  Google Scholar 

  19. Meemken F, Baiker A (2017) Chem Rev 117:11522

    Article  CAS  PubMed  Google Scholar 

  20. Tang Z (2018) Chiral nanomaterials: preparation, properties and applications. Wiley, Hoboken

    Book  Google Scholar 

  21. Maeda N, Hungerbühler K, Baiker A (2011) J Am Chem Soc 133:19567

    Article  CAS  PubMed  Google Scholar 

  22. Meemken F, Maeda N, Hungerbuehler K, Baiker A (2012) Angew Chem Int Ed 51:8212

    Article  CAS  Google Scholar 

  23. Goubert G, McBreen PH (2013) ChemCatChem 5:683

    Article  CAS  Google Scholar 

  24. Crabtree RH (2012) Chem Rev 112:1536

    Article  CAS  PubMed  Google Scholar 

  25. Demers-Carpentier V, Goubert G, Masini F, Lafleur-Lambert R, Dong Y, Lavoie S, Mahieu G, Boukouvalas J, Gao H, Rasmussen AMH, Ferrighi L, Pan Y, Hammer B, McBreen PH (2011) Science 334:6057

    Article  CAS  Google Scholar 

  26. Orglmeister E, Mallat T, Baiker A (2005) Adv Synth Catal 347:78

    Article  CAS  Google Scholar 

  27. Dong Y, Svane K, Lemay JC, Groves MN, McBreen PH (2017) ACS Catal 7:1757

    Article  CAS  Google Scholar 

  28. Goubert G, Dong Y, Groves MN, Lemay JC, Hammer B, McBreen PH (2017) Nat Chem 9:531

    Article  CAS  PubMed  Google Scholar 

  29. Lavoie S, Laliberté M-A, Temprano I, McBreen PH (2006) J Am Chem Soc 128:7588

    Article  CAS  PubMed  Google Scholar 

  30. Studer M, Burkhardt S, Blaser H-U (1999) Chem Commun:1727

    Google Scholar 

  31. von Arx M, Mallat T, Baiker A (2002) Catal Lett 78:267

    Article  Google Scholar 

  32. Diezi S, Hess M, Orglmeister E, Mallat T, Baiker A (2005) Catal Lett 102:121

    Article  CAS  Google Scholar 

  33. Yang HP, Wang H, Lu JX (2015) Electrochem Commun 55:18

    Article  CAS  Google Scholar 

  34. Yang HP, Fen Q, Wang H, Lu JX (2016) Electrochem Commun 71:38

    Article  CAS  Google Scholar 

  35. Yue YN, Wu D, Zeng S, Yang MP, Wang H, Lu JX (2017) New J Chem 41:7853

    Article  CAS  Google Scholar 

  36. Zhu J, Sun X-T, Wang X-D, Wu L (2018) ChemCatChem 10:1788

    Article  CAS  Google Scholar 

  37. Tungler A, Tarnai T, Máthé T, Petró J (1991) J Mol Catal 67:277

    Article  CAS  Google Scholar 

  38. Perosa A, Tundo P, Selva M (2002) J Mol Catal A Chem 180:169

    Article  CAS  Google Scholar 

  39. Vetere V, Faraoni MB, Santori GF, Podestá J, Casella ML, Ferretti OA (2004) J Catal 226:457

    Article  CAS  Google Scholar 

  40. Vetere V, Faraoni MB, Santori GF, Podestá JC, Casella ML, Ferretti OA (2005) Catal Today 107–108:266

    Article  CAS  Google Scholar 

  41. Cheng H, Hao J, Wang H, Xi C, Meng X, Cai S, Zhao F (2007) J Mol Catal A Chem 278:6

    Article  CAS  Google Scholar 

  42. Wang J, Feng H, Qin R, Fu H, Yuan M, Chen H, Li X (2007) Tetrahedron Asymmetry 18:1643

    Article  CAS  Google Scholar 

  43. Jiang HY, Yang CF, Li C, Fu HY, Chen H, Li RX, Li XJ (2008) Angew Chem Int Ed 47:9240

    Article  CAS  Google Scholar 

  44. Jiang H-Y, Sun B, Zheng X-X, Chen H (2012) Appl Catal A 421:86

    Article  CAS  Google Scholar 

  45. Li C, Zhang L, Zheng C, Zheng X, Fu H, Chen H, Li R (2014) Tetrahedron Asymmetry 25:821

    Article  CAS  Google Scholar 

  46. Yang CF, Jiang HY, Feng J, Fu HY, Li RX, Chen H, Li XJ (2009) J Mol Catal A Chem 300:98

    Article  CAS  Google Scholar 

  47. Li C, Zhang L, Liu H, Zheng X, Fu H, Chen H, Li R (2014) Catal Commun 54:27

    Article  CAS  Google Scholar 

  48. Jiang H-Y, Chen H, Li R-X (2010) Catal Commun 11:584

    Article  CAS  Google Scholar 

  49. Tungler A, Kajtar M, Mathe T, Toth G, Fogassy E, Petro J (1989) Catal Today 5:159

    Article  CAS  Google Scholar 

  50. Tungler A, Máthé T, Petró J, Tarnai T (1990) J Mol Catal 61:259

    Article  CAS  Google Scholar 

  51. McIntosh AI, Watson DJ, Burton JW, Lambert RM (2006) J Am Chem Soc 128:7329

    Article  CAS  PubMed  Google Scholar 

  52. Mhadgut SC, Török M, Dasgupta S, Török B (2008) Catal Lett 123:156

    Article  CAS  Google Scholar 

  53. Watson DJ, Jesudason RJBRJ, Beaumont SK, Kyriakou G, Burton JW, Lambert RM (2009) J Am Chem Soc 131:14584

    Article  CAS  PubMed  Google Scholar 

  54. Mhadgut SC, Török M, Esquibel J, Török B (2006) J Catal 238:441

    Article  CAS  Google Scholar 

  55. Schafer C, Mhadgut SC, Kugyela N, Torok M, Torok B (2015) Cat Sci Technol 5:716

    Article  CAS  Google Scholar 

  56. Rodríguez-García L, Hungerbühler K, Baiker A, Meemken F (2015) J Am Chem Soc 137:12121

    Article  PubMed  CAS  Google Scholar 

  57. Kunz S, Schreiber P, Ludwig M, Maturi MM, Ackermann O, Tschurl M, Heiz U (2013) Phys Chem Chem Phys 15:19253

    Article  CAS  PubMed  Google Scholar 

  58. Schrader I, Warneke J, Backenköhler J, Kunz S (2015) J Am Chem Soc 137:905

    Article  CAS  PubMed  Google Scholar 

  59. Schrader I, Neumann S, Himstedt R, Zana A, Warneke J, Kunz S (2015) Chem Commun 51:16221

    Article  CAS  Google Scholar 

  60. Schrader I, Neumann S, Sulce A, Schmidt F, Azov V, Kunz S (2017) ACS Catal 7:3979

    Article  CAS  Google Scholar 

  61. Šulce A, Backenköhler J, Schrader I, Piane MD, Müller C, Wark A, Ciacchi LC, Azov V, Kunz S (2018) Cat Sci Technol 8:6062

    Article  Google Scholar 

  62. Gross E, Liu JH, Alayoglu S, Marcus MA, Fakra SC, Toste FD, Somorjai GA (2013) J Am Chem Soc 135:3881

    Article  CAS  PubMed  Google Scholar 

  63. Tang W, Zhang X (2003) Chem Rev 103:3029

    Article  CAS  PubMed  Google Scholar 

  64. Li YM, Kwong FY, Yu WY, Chan ASC (2007) Coord Chem Rev 251:2119

    Article  CAS  Google Scholar 

  65. Pereira MM, Calvete MJF, Carrilho RMB, Abreu AR (2013) Chem Soc Rev 42:6990

    Article  CAS  PubMed  Google Scholar 

  66. Mikhailine A, Lough AJ, Morris RH (2009) J Am Chem Soc 131:1394

    Article  CAS  PubMed  Google Scholar 

  67. Meyer N, Lough AJ, Morris RH (2009) Chem Eur J 15:5605

    Article  CAS  PubMed  Google Scholar 

  68. Sonnenberg JF, Morris RH (2014) Cat Sci Technol 4:3426

    Article  CAS  Google Scholar 

  69. Sonnenberg JF, Coombs N, Dube PA, Morris RH (2012) J Am Chem Soc 134:5893

    Article  CAS  PubMed  Google Scholar 

  70. Prokopchuk DE, Sonnenberg JF, Meyer N, Zimmer-De Iuliis M, Lough AJ, Morris RH (2012) Organometallics 31:3056

    Article  CAS  Google Scholar 

  71. Li Y, Yu S, Wu X, Xiao J, Shen W, Dong Z, Gao J (2014) J Am Chem Soc 136:4031

    Article  CAS  PubMed  Google Scholar 

  72. Cano I, Tschan MJL, Martinez-Prieto LM, Philippot K, Chaudret B, van Leeuwen P (2016) Cat Sci Technol 6:3758

    Article  CAS  Google Scholar 

  73. Xia YT, Ma J, Wang XD, Yang L, Wu L (2017) Cat Sci Technol 7:5515

    Article  CAS  Google Scholar 

  74. Riant O, Mostefai N, Courmarcel J (2004) Synthesis:2943

    Google Scholar 

  75. Tamura M, Fujihara H (2003) J Am Chem Soc 125:15742

    Article  CAS  PubMed  Google Scholar 

  76. Kantam ML, Laha S, Yadav J, Likhar PR, Sreedhar B, Choudary BM (2007) Adv Synth Catal 349:1797

    Article  CAS  Google Scholar 

  77. Kantam ML, Yadav J, Laha S, Srinivas P, Sreedhar B, Figueras F (2009) J Org Chem 74:4608

    Article  CAS  PubMed  Google Scholar 

  78. Li M, Li B, Xia H-F, Ye D, Wu J, Shi Y (2014) Green Chem 16:2680

    Article  CAS  Google Scholar 

  79. Akiyama R, Kobayashi S (2001) Angew Chem Int Ed 40:3469

    Article  CAS  Google Scholar 

  80. Jansat S, Gómez M, Philippot K, Muller G, Guiu E, Claver C, Castillon S, Chaudret B (2004) J Am Chem Soc 126:1592

    Article  CAS  PubMed  Google Scholar 

  81. Favier I, Gómez M, Muller G, Axet MR, Castillon S, Claver C, Jansat S, Chaudret B, Philippot K (2007) Adv Synth Catal 349:2459

    Article  CAS  Google Scholar 

  82. Dieguez M, Pamies O, Mata Y, Teuma E, Gomez M, Ribaudo F, van Leeuwen PWNM (2008) Adv Synth Catal 350:2583

    Article  CAS  Google Scholar 

  83. Felpin FX, Landais Y (2005) J Org Chem 70:6441

    Article  CAS  PubMed  Google Scholar 

  84. Reimann S, Mallat T, Baiker A (2007) J Catal 252:30

    Article  CAS  Google Scholar 

  85. Reimann S, Mallat T, Baiker A (2008) J Catal 254:79

    Article  CAS  Google Scholar 

  86. Reimann S, Grunwaldt J-D, Mallat T, Baiker A (2010) Chem Eur J 16:9658

    Article  CAS  PubMed  Google Scholar 

  87. Sawai K, Tatumi R, Nakahodo T, Fujihara H (2008) Angew Chem Int Ed 47:6917

    Article  CAS  Google Scholar 

  88. Mori K, Kondo Y, Yamashita H (2009) Phys Chem Chem Phys 11:8949

    Article  CAS  PubMed  Google Scholar 

  89. Klosin J, Landis CR (2007) Acc Chem Res 40:1251

    Article  CAS  PubMed  Google Scholar 

  90. Neves ACB, Calvete MJF, Melo T, Pereira MM (2012) Eur J Org Chem:6309

    Google Scholar 

  91. Coronado JM, Coloma F, Anderson JA (2000) J Mol Catal A Chem 154:143

    Article  CAS  Google Scholar 

  92. Han D, Li X, Zhang H, Liu Z, Li J, Li C (2006) J Catal 243:318

    Article  CAS  Google Scholar 

  93. Han D, Li X, Zhang H, Liu Z, Hu G, Li C (2008) J Mol Catal A Chem 283:15

    Article  CAS  Google Scholar 

  94. Axet MR, Castillon S, Claver C, Philippot K, Lecante P, Chaudret B (2008) Eur J Inorg Chem 2008:3460

    Article  CAS  Google Scholar 

  95. Alsalahi W, Trzeciak AM (2018) ChemistrySelect 3:1727

    Article  CAS  Google Scholar 

  96. Park KH, Chung YK (2005) Adv Synth Catal 347:854

    Article  CAS  Google Scholar 

  97. Chen MY, Xu Z, Chen L, Song T, Zheng ZJ, Cao J, Cui YM, Xu LW (2018) ChemCatChem 10:280

    Article  CAS  Google Scholar 

  98. Hopkinson MN, Richter C, Schedler M, Glorius F (2014) Nature 510:485

    Article  CAS  PubMed  Google Scholar 

  99. Zhukhovitskiy AV, MacLeod MJ, Johnson JA (2015) Chem Rev 115:11503

    Article  CAS  PubMed  Google Scholar 

  100. Ranganath KVS, Kloesges J, Schäfer AH, Glorius F (2010) Angew Chem Int Ed 49:7786

    Article  CAS  Google Scholar 

  101. Richter C, Ranganath KVS, Glorius F (2012) Adv Synth Catal 354:377

    Article  CAS  Google Scholar 

  102. Ranganath KVS, Schaefer AH, Glorius F (2011) ChemCatChem 3:1889

    Article  CAS  Google Scholar 

  103. Ye R, Zhukhovitskiy AV, Kazantsev RV, Fakra SC, Wickemeyer BB, Toste FD, Somorjai GA (2018) J Am Chem Soc 140:4144

    Article  CAS  PubMed  Google Scholar 

  104. Shu X-Z, Nguyen SC, He Y, Oba F, Zhang Q, Canlas C, Somorjai GA, Alivisatos AP, Toste FD (2015) J Am Chem Soc 137:7083

    Article  CAS  PubMed  Google Scholar 

  105. Hayashi T, Ueyama K, Tokunaga N, Yoshida K (2003) J Am Chem Soc 125:11508

    Article  CAS  PubMed  Google Scholar 

  106. Fischer C, Defieber C, Suzuki T, Carreira EM (2004) J Am Chem Soc 126:1628

    Article  CAS  PubMed  Google Scholar 

  107. Defieber C, Gruetzmacher H, Carreira EM (2008) Angew Chem Int Ed 47:4482

    Article  CAS  Google Scholar 

  108. Dong HQ, Xu MH, Feng CG, Sun XW, Lin GQ (2015) Org Chem Front 2:73

    Article  CAS  Google Scholar 

  109. Nagamoto M, Nishimura T (2017) ACS Catal 7:833

    Article  CAS  Google Scholar 

  110. Hayashi T, Yamasaki K (2003) Chem Rev 103:2829

    Article  CAS  PubMed  Google Scholar 

  111. Takaya Y, Ogasawara M, Hayashi T, Sakai M, Miyaura N (1998) J Am Chem Soc 120:5579

    Article  CAS  Google Scholar 

  112. Tian P, Dong H-Q, Lin G-Q (2012) ACS Catal 2:95

    Article  CAS  Google Scholar 

  113. Howell GP (2012) Org Process Res Dev 16:1258

    Article  CAS  Google Scholar 

  114. Brock S, Hose D, Moseley J, Parker A, Patel I, Williams A (2008) Org Process Res Dev 12:496

    Article  CAS  Google Scholar 

  115. Yasukawa T, Miyamura H, Kobayashi S (2012) J Am Chem Soc 134:16963

    Article  CAS  PubMed  Google Scholar 

  116. Yasukawa T, Suzuki A, Miyamura H, Nishino K, Kobayashi S (2015) J Am Chem Soc 137:6616

    Article  CAS  PubMed  Google Scholar 

  117. Satyanarayana T, Abraham S, Kagan HB (2009) Angew Chem Int Ed 48:456

    Article  CAS  Google Scholar 

  118. Miyamura H, Suzuki A, Yasukawa T, Kobayashi S (2015) Adv Synth Catal 357:3815

    Article  CAS  Google Scholar 

  119. Kobayashi S, Miyamura H (2013) Aldrichimica Acta 46:3

    CAS  Google Scholar 

  120. Yasukawa T, Miyamura H, Kobayashi S (2015) Chem Sci 6:6224

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  121. Kobayashi S, Akiyama R, Furuya T, Moriwaki M (1998) Molecules 2:35

    Article  CAS  Google Scholar 

  122. Yasukawa T, Saito Y, Miyamura H, Kobayashi S (2016) Angew Chem Int Ed 55:8058

    Article  CAS  Google Scholar 

  123. Yasukawa T, Kuremoto T, Miyamura H, Kobayashi S (2016) Org Lett 18:2716

    Article  CAS  PubMed  Google Scholar 

  124. Miyamura H, Nishino K, Yasukawa T, Kobayashi S (2017) Chem Sci 8:8362

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  125. Hadian-Dehkordi L, Hosseini-Monfared H (2016) Green Chem 18:497

    Article  CAS  Google Scholar 

  126. Kaushik M, Basu K, Benoit C, Cirtiu CM, Vali H, Moores A (2015) J Am Chem Soc 137:6124

    Article  CAS  PubMed  Google Scholar 

  127. Hao B, Gunaratna MJ, Zhang M, Weerasekara S, Seiwald SN, Nguyen VT, Meier A, Hua DH (2016) J Am Chem Soc 138:16839

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  128. Takale BS, Bao M, Yamamoto Y (2014) Org Biomol Chem 12:2005

    Article  CAS  PubMed  Google Scholar 

  129. Ma HC, Kan JL, Chen GJ, Chen CX, Dong YB (2017) Chem Mater 29:6518

    Article  CAS  Google Scholar 

  130. Sharma P, Sharma RK (2017) ChemistrySelect 2:513

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Shū Kobayashi .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2020 Springer Nature Switzerland AG

About this chapter

Check for updates. Verify currency and authenticity via CrossMark

Cite this chapter

Yasukawa, T., Kobayashi, S. (2020). Chiral Metal Nanoparticles for Asymmetric Catalysis. In: Kobayashi, S. (eds) Nanoparticles in Catalysis. Topics in Organometallic Chemistry, vol 66. Springer, Cham. https://doi.org/10.1007/3418_2020_39

Download citation

Publish with us

Policies and ethics