Skip to main content
SpringerLink
Log in

Thiourea Based Fluorous Organocatalyst

  • Chapter
  • First Online:
Fluorous Chemistry

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 308))

Abstract

This review deals with general and significant development of the fluorous organocatalysts based on thiourea. The applications of fluorous technology are briefly discussed. The implementations of thiourea based catalysts in organic synthesis are focused on in the chapter.

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

Access this chapter

Log in via an institution
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

Notes

  1. 1.

    http://www.fluorous.com

References

  1. Houk KN, List B (2004) Asymmetric organocatalysis. Acc Chem Res 37:487

    Article  CAS  Google Scholar 

  2. List B (2007) Introduction: organocatalysis. Chem Rev 107:5413

    Article  CAS  Google Scholar 

  3. Seayad J, List B (2005) Asymmetric organocatalysis. Org Biomol Chem 3:719

    Article  CAS  Google Scholar 

  4. Dalko PI, Moisan L (2001) Enantioselective organocatalysis. Angew Chem Int Ed Engl 40:3726

    Article  CAS  Google Scholar 

  5. Dalko PI, Moisan L (2004) In the golden age of organocatalysis. Angew Chem Int Ed Engl 43:5138

    Article  CAS  Google Scholar 

  6. Notz W, Tanaka F, Barbas CF (2004) Enamine-based organocatalysis with proline and diamines: the development of direct catalytic asymmetric Aldol, Mannich, Michael, and Diels-Alder reactions. Acc Chem Res 37:580

    Article  CAS  Google Scholar 

  7. Chen YG, Tian SK, Deng L (2000) A highly enantioselective catalytic desymmetrization of cyclic anhydrides with modified cinchona alkaloids. J Am Chem Soc 122:9542

    Article  CAS  Google Scholar 

  8. Jarvo ER, Miller SJ (2002) Amino acids and peptides as asymmetric organocatalysts. Tetrahedron 58:2481

    Article  CAS  Google Scholar 

  9. Yamada YMA, Ikegami S (2000) Efficient Baylis–Hillman reactions promoted by mild cooperative catalysts and their application to catalytic asymmetric synthesis. Tetrahedron Lett 41:2165

    Article  CAS  Google Scholar 

  10. Schreiner PR (2003) Metal-free organocatalysis through explicit hydrogen bonding interactions. Chem Soc Rev 32:289

    Article  CAS  Google Scholar 

  11. Zhang W, Curran DP (2006) Synthetic applications of fluorous solid-phase extraction (F-SPE). Tetrahedron 62:11837

    Article  CAS  Google Scholar 

  12. Etter MC (1990) Encoding and decoding hydrogen-bond patterns of organic compounds. Acc Chem Res 23:120

    Article  CAS  Google Scholar 

  13. Etter MC, Panunto TW (1988) 1,3-Bis(m-nitrophenyl)urea: an exceptionally good complexing agent for proton acceptors. J Am Chem Soc 110:5896

    Article  CAS  Google Scholar 

  14. Curran DP, Kuo LH (1994) Structure-based analysis and optimization of a highly enantioselective catalyst for the Strecker reaction. J Org Chem 59:3259

    Article  CAS  Google Scholar 

  15. Curran DP, Kuo LH (1995) Acceleration of a dipolar Claisen rearrangement by hydrogen bonding to a soluble diaryl-urea. Tetrahedron Lett 36:6647

    CAS  Google Scholar 

  16. Sigman MS, Jacobsen EN (1998) Schiff base catalysts for the asymmetric Strecker reaction identified and optimized from parallel synthetic libraries. J Am Chem Soc 120:4901

    Article  CAS  Google Scholar 

  17. Sigman MS, Vachal P, Jacobsen EN (2000) Angew Chem Int Ed Engl 112:1336

    Article  Google Scholar 

  18. Vachal P, Jacobsen EN (2002) Structure-based analysis and optimization of a highly enantioselective catalyst for the Strecker reaction. J Am Chem Soc 124:10012

    Article  CAS  Google Scholar 

  19. Wenzel AG, Jacobsen EN (2002) Asymmetric catalytic Mannich reactions catalyzed by urea derivatives: enantioselective synthesis of β-aryl-β-amino acids. J Am Chem Soc 124:12964

    Article  CAS  Google Scholar 

  20. Okino T, Hoashi Y, Takemoto Y (2003) Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts. J Am Chem Soc 125:12672

    Article  CAS  Google Scholar 

  21. Okino T, Hoashi Y, Furukawa T, Xu X, Takemoto Y (2005) Enantio- and diastereoselective Michael reaction of 1,3-dicarbonyl compounds to nitroolefins catalyzed by a bifunctional thiourea. J Am Chem Soc 127:119

    Article  CAS  Google Scholar 

  22. Yamaoka T, Miyabe H, Takemoto Y (2007) Catalytic enantioselective Petasis-type reaction of quinolines catalyzed by a newly designed thiourea catalyst. J Am Chem Soc 129:6686

    Article  CAS  Google Scholar 

  23. Inokuma T, Hoashi Y, Takemoto Y (2006) Thiourea-catalyzed asymmetric Michael addition of activated methylene compounds to α, β-unsaturated imides: dual activation of imide by intra- and intermolecular hydrogen bonding. J Am Chem Soc 128:9413

    Article  CAS  Google Scholar 

  24. Miyabe H, Takemoto Y (2008) Discovery and application of asymmetric reaction by multi-functional thioureas. Bull Chem Soc Jpn 81:785

    Article  CAS  Google Scholar 

  25. Cao C, Ye M, Sun X, Tang Y (2006) Pyrrolidine-thiourea as a bifunctional organocatalyst: highly enantioselective Michael addition of cyclohexanone to nitroolefins. Org Lett 8:2901

    Article  CAS  Google Scholar 

  26. Dahlin N, Bφgevig A, Adolfsson H (2004) Adv Synth Catal 346:1101

    Article  CAS  Google Scholar 

  27. Wang J, Li H, Yu X, Zu L, Wang W (2005) Chiral binaphthyl-derived amine-thiourea organocatalyst-promoted asymmetric Morita-Baylis-Hillman reaction. Org Lett 7:4293

    Article  CAS  Google Scholar 

  28. Wang J, Li H, Duan W, Zu L, Wang W (2005) Organocatalytic asymmetric Michael addition of 2,4-pentandione to nitroolefins. Org Lett 7:4713

    Article  CAS  Google Scholar 

  29. McCooey SH, Connon SJ (2005) Urea- and thiourea-substituted cinchona alkaloid derivatives as highly efficient bifunctional organocatalysts for the asymmetric addition of malonate to nitroalkene: inversion of configuration at C9 dramatically improves catalyst performance. Angew Chem Int Ed Engl 44:6367

    Article  CAS  Google Scholar 

  30. Vakulya B, Varga S, Csampai A, Soós T (2005) Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts. Org Lett 7:1967

    Article  CAS  Google Scholar 

  31. Hideto M, Tuchida S, Yamauchi M, Takemoto Y (2006) Reaction of nitroorganic compounds using thiourea catalysts anchored to polymer support. Synthesis 19:3295

    Google Scholar 

  32. Mike K, Schreiner P (2007) Generally applicable organocatalytic tetrahydropyranylation of hydroxy functionalities with very low catalyst loading. Synthesis 5:779

    Google Scholar 

  33. Lukas W, Cabrele C, Vanejews M, Schreiner PR (2007) γ-Aminoadamantanecarboxylic acids through direct C-H bond amidations. European J Org Chem 9:1474

    Google Scholar 

  34. Liu K, Cui H, Nie J, Dong K et al (2007) Highly enantioselective Michael addition of aromatic ketones to nitroolefins promoted by chiral bifunctional primary amine-thiourea catalysts based on saccharides. Org Lett 9:923

    Article  CAS  Google Scholar 

  35. Li X, Liu K, Ma H, Nie J et al (2008) Highly enantioselective michael addition of malonates to nitroolefins catalyzed by chiral bifunctional tertiary amine-thioureas based on saccharides. Synlett 20:3242

    Google Scholar 

  36. Schreiner PR, Wittkopp A (2002) H-Bonding additives act like Lewis acid catalysts. Org Lett 4:217

    Article  CAS  Google Scholar 

  37. Kote M, Schreiner PR (2006) Acid-free, organocatalytic acetalization. Tetrahedron 62:434

    Article  Google Scholar 

  38. Yu MS, Curran DP, Nagashima T (2005) Increasing fluorous partition coefficients by solvent tuning. Org Lett 7:3677

    Article  CAS  Google Scholar 

  39. Huang YB, Yi WB, Cai C (2010) An efficient, recoverable fluorous organocatalyst for direct reductive amination of aldehydes. J Fluor Chem 131:879

    Article  CAS  Google Scholar 

  40. Berkessel A, Seelig B (2009) A simplified synthesis of Takemoto’s catalyst. Synlett 2113

    Google Scholar 

  41. Wang L, Cai C, Curran DP, Zhang W (2010) Enantioselective α-chlorination of aldehydes with recyclable fluorous (S)-pyrrolidine-thiourea bifunctional organocatalyst. Synlett 433

    Google Scholar 

  42. Pipko PM (2004) Activation of carbonyls by double hydrogen bonding: an emerging tool in asymmetric catalysis. Angew Chem Int Ed Engl 43:2062

    Article  Google Scholar 

  43. Wittkopp A, Schreiner PR (2003) Metal-free, noncovalent catalysis of Diels–Alder reactions by neutral hydrogen bond donors in organic solvents and in water. Chemistry 9:407

    Article  CAS  Google Scholar 

  44. Sohtome Y, Takemura N, Takagi R et al (2008) Thiourea-catalyzed Morita–Baylis–Hillman reaction. Tetrahedron 64:9423

    Article  CAS  Google Scholar 

  45. Huang YB, Yi WB, Cai C. An efficient, recoverable fluorous organocatalyst for accelerating the DABCO-promoted Morita-Baylis-Hillman reaction. Chin Chem Lett. doi:10.1016/j.cclet.2011.03.010

  46. Dessole G, Herrera RP, Ricci A (2004) H-Bonding organocatalysed Friedel-Crafts alkylation of aromatic and heteroaromatic systems with nitroolefins. Synlett 2374

    Google Scholar 

  47. Dömling A, Ugi I (2000) Multicomponent reactions with isocyanides. Angew Chem Int Ed Engl 39:3168

    Article  Google Scholar 

  48. Ramón DJ, Yus M (2005) Asymmetric multicomponent reactions: the new frontier. Angew Chem Int Ed Engl 44:1602

    Article  Google Scholar 

  49. Pan SC, List B (2007) Catalytic one-pot, three-component acyl-Strecker reaction. Synlett 318

    Google Scholar 

  50. Tararov VI, Kadyrov R, Riermeier TH et al (2004) Direct reductive amination versus hydrogenation of intermediates - a comparison. Adv Synth Catal 346:561

    Article  CAS  Google Scholar 

  51. Gross T, Seayad AM, Ahmad M, Beller M (2002) Synthesis of primary amines: first homogeneously catalyzed reductive amination with ammonia. Org Lett 4:2055

    Article  CAS  Google Scholar 

  52. Miriyala B, Bhattacharyya S, Williamson JS (2004) Tetrahedron 60:1463

    Article  CAS  Google Scholar 

  53. Itoh T, Nagata K, Ishikawa H et al (2004) A selective reductive amination of aldehydes by the use of Hantzsch dihydropyridines as reductant. Tetrahedron 60:6649

    Article  CAS  Google Scholar 

  54. Weil T, Kotke M, Kleiner CM, Schreiner PR (2008) Cooperative brønsted acid-type organocatalysis: alcoholysis of styrene oxides. Org Lett 10:1513

    Article  CAS  Google Scholar 

  55. Halland N, Braunton A, Bachmann S et al (2004) Direct organocatalytic asymmetric α-chlorination of aldehydes. J Am Chem Soc 126:4790

    Article  CAS  Google Scholar 

  56. Brochu MP, Brown SP, MacMillan DWC (2004) Direct and enantioselective organocatalytic α-chlorination of aldehydes. J Am Chem Soc 126:4108

    Article  CAS  Google Scholar 

  57. Mei Y, Bentley PA, Du J (2009) NCS with thiourea as highly efficient catalysts for acetalization of aldehydes. Tetrahedron Lett 50:4199

    Article  CAS  Google Scholar 

  58. Spencer CM, Faulds D (2000) Esomeprazole. Drugs 60:321

    Article  CAS  Google Scholar 

  59. Russo A, Lattanzi A (2009) Hydrogen-bonding catalysis: mild and highly chemoselective oxidation of sulfides. Adv Synth Catal 351:521

    Article  CAS  Google Scholar 

  60. Mba M, Prins LJ, Licini G (2007) C3-Symmetric Ti(IV) triphenolate amino complexes as sulfoxidation catalysts with aqueous hydrogen peroxide. Org Lett 9:21

    Article  CAS  Google Scholar 

  61. Huang YB, Yi WB, Cai C (2011) A recyclable fluorous thiourea organocatalyst for the chemoselective oxidation of sulfides. J Fluorine Chem. doi:10.1016/j.jfluchem.2011.05.026

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Nanjing University of Science and Technology, Nanjing, P.R. China

    Yi-Bo Huang, Wen-Bin Yi & Chun Cai

Authors
  1. Yi-Bo Huang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Wen-Bin Yi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Chun Cai
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Chun Cai .

Editor information

Editors and Affiliations

  1. , Department of Biology and Chemistry, City University of Hong Kong, Tat Chee Avenue, Kowloon, China, People's Republic

    István T. Horváth

Rights and permissions

Reprints and permissions

Copyright information

© 2011 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Huang, YB., Yi, WB., Cai, C. (2011). Thiourea Based Fluorous Organocatalyst. In: Horváth, I. (eds) Fluorous Chemistry. Topics in Current Chemistry, vol 308. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2011_248

Download citation

Publish with us

Policies and ethics

Search

Navigation