(S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine – an effective catalyst of asymmetric synthesis

Authors

  • V. M. Tkachuk Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • V. M. Shoba Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • V. A. Sukach Institute of Organic Chemistry of the NAS of Ukraine, Ukraine
  • M. V. Vovk Institute of Organic Chemistry of the NAS of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.14.784

Keywords:

asymmetric organocatalyst, (S)-( )-1-(pyrrolidinylmethyl)-pyrrolidine, aldol condensation, Michael reaction, Mannich reaction (S)-( )-1-(2-pyrrolidinylmethyl)pyrrolidine – an effective catalyst of asymmetric synthesis

Abstract

The literature sources concerning application of 1-(pyrrolidin-2 ylmethyl)pyrrolidine as an effective organocatalyst of asymmetric reactions have been reviewed and systematized. The role of the tertiary amine fragment in the structure of the catalyst has been emphasized; it makes an asymmetric arrangement in the transition state of the key step during the new C-C bond formation. The importance of Bronsted acid as a promoter (additive), which protonates the basic nitrogen atom transforming it to the N-H-donor system, has been noted. Aldol condensation catalyzed by 1-(pyrrolidinyl-2-ylmethyl)pyrrolidine that can be undoubtedly considered as one the most valuable tools in asymmetric synthesis and construction of various optically active organic frameworks has been reviewed in details. A powerful catalytic activity of 1-(pyrrolidinyl-2-ylmethyl)pyrrolidine in the Mannich reaction leading to a new C-C bond and chiral centre creation has been demonstrated. A significant attention in the review is devoted to application of 1-(pyrrolidin-2-ylmethyl)pyrrolidine in the asymmetric version of the Mannich reaction as a convenient approach for the synthesis of chiral β-aminoketones and β-aminoesters being well known as useful building blocks and precursors for important nitrogen-containing natural products and heterocycles.

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References

  1. Ahrendt K. A., Borths C. J., MacMillan D. W. J. of the American Chemical Society, 2000, Vol. 122, No.17, pp.4243-4244.
  2. Mukherjee S., Yang J. W., Hoffmann S., List B. Chemical Reviews, 2007, Vol. 107, No.12, pp.5471-5569.
  3. Meninno S., Lattanzi A. Chemical Communications, 2013, Vol. 49, No.37, pp.3821-3832.
  4. Aleman J., Cabrera S. Chemical Society Rev., 2013, Vol. 42, No.2, pp.774-793.
  5. Cahard D., Xu X., Couve-Bonnaire S., Pannecoucke X. Chemical Society Reviews, 2010, Vol. 39, No.2, pp.558-568.
  6. Yu X., Wang W. Organic and Biomolecular Chemistry, 2008, Vol. 6, No.12, pp.2037-2046.
  7. Xu L. V., Lu Y. Organic and Biomolecular Chemistry, 2008, Vol. 6, No.12, pp.2047-2053.
  8. Sulzer-Mosse S., Alexakis A. Chemical Communications, 2007, Vol. 14, No.30, pp.3123-3135.
  9. Brazier J. B., Tomkinson N. C. O. In Topics in Current Chemistry, B. List (Ed.). – Springer, 2010, pp.281-348.
  10. Sone T., Hiroi K., Yamada S. Chemical Pharmaceutical Bulletin, 1973, Vol. 21, No.10, pp.2331-2335.
  11. Saito S., Nakadai M., Yamamoto H. Synlett, 2001, Vol. 8, pp.1245-1248.
  12. Nakadai M., Saito S., Yamamoto H. Tetrahedron, 2002, Vol. 58, No.41, pp.8167-8178.
  13. Cordova A., Notz W., Barbas C. F. Chemical Communication, 2002, Vol. 24, pp.3024-3025.
  14. Saito S., Yamamoto H. Accounts of Chemical Research, 2004, Vol. 37, No.8, pp.570-579.
  15. Mase Nobuyuki, Tanaka Fujie, Barbas Carlos F. Angewandte Chemie International Edition, 2004, Vol. 43, No.18, pp.2420-2423.
  16. Catalan-Munoz S., Muller C. A., Ley S. V. Eur. J. of Org. Chem., 2010, Vol. 1, pp.183-190.
  17. Albrecht L., Deredas D., Wojciechowski J. et al. Synthesis, 2012, Vol. 44, No.2, pp.247-252.
  18. Bui Tommy, Barbas Carlos F. Tetrahedron Lett., 2000, Vol. 41, No.36, pp.6951-6954.
  19. Akahane Yuichi, Inomata Kohei, Endo Yasuyuki Heterocycles, 2011, Vol. 82, No.2, pp.1727-1737.
  20. Dambruoso P., Massi A., Dondoni A. Organic Lett., 2005, Vol. 7, No.21, pp.4657-4660.
  21. Betancort Juan M., Sakthivel Kandasamy, Thayumanavan Rajeswari, Tanaka Fujie, Barbas Carlos F. Synthesis, 2004, Vol. 9, pp.1509-1521.
  22. Mase Nobuyuki, Thayumanavan Rajeswari, Tanaka Fujie, Barbas Carlos F. Organic Lett., 2004, Vol. 6, No.15, pp.2527-2530.
  23. Belot Sebastien, Sulzer-Mosse Sarah, Kehrli Stefan, Alexakis Alexandre Chemical Communication, 2008, Vol. 39, pp.4694-4696.
  24. Belot Sebastien, Quintard Adrien, Alexakis Alexandre, Krause Norbert, Advanced Synthesis and Catalysis, 2010, Vol. 352, No.4, pp.667-695.
  25. Ramachary Dhevalapally B., Sakthidevi Rajasekar Organic and Biomolecular Chem., 2010, Vol. 8, No.19, pp.4259-4265.
  26. Zhang Xinshuai, Zhang Shilei, Wang Wei Angewandte Chemie International Edition, 2010, Vol. 49, No.8, pp.1481-1484.
  27. Felluga F., Forzato C., Nitti P. et al. Chirality, 2012, Vol. 24, pp.1005-1012.
  28. Betancort Juan M., Sakthivel Kandasamy, Thayumanavan Rajeswari, Barbas Carlos F. Tetrahedron Lett., 2001, Vol. 42, No.27, pp.4441-4444.
  29. Chowdhury Raghunath, Ghosh Sunil K. Organic Lett., 2009, Vol. 11, No.15, pp.3270-3273.
  30. Chowdhury Raghunath, Ghosh Sunil K. Synthesis, 2011, Vol. 12. pp.1936-1945.
  31. Pitacco G., Felluga F., Forzato C., Nitti P., Valentin Ennio, Zangrando Ennio, Attanasi Orazio A., Lucia De Crescentini, Favi Gianfranco, Mantellini
  32. Fabio Tetrahedron: Asymmetry, 2010, Vol. 21, No.5, pp.617-622.
  33. Barros Maria Teresa, Phillips Ana Maria Faisca Eur. J. of Org. Chem., 2008, Vol. 15, pp.2525-2529.
  34. Faisca Phillips Ana Maria, Barros Maria Teresa Organic and Biomolecular Chem., 2012, Vol. 10, No.2, pp.404-412.
  35. Rios Ramon, Sunden Henrik, Ibrahem Ismail, Zhao Gui-Ling, Cordova Armando Tetrahedron Lett., 2006, Vol. 47, No.49, pp.8679-8682.
  36. Rios Ramon, Sunden Henrik, Ibrahem Ismail, Cordova Armando Tetrahedron Lett., 2007, Vol. 48, No.12, pp.2181-2184.
  37. Wolfgang Notz, Kandasamy Sakthivel, Tommy Bui, Guofu Zhong and Carlos Barbas F. Tetrahedron Lett., 2001, Vol. 42, No.2, pp.99-201.
  38. Zhuang Wei, Saaby Steen, Jorgensen K. A. Angewantde Chemie International Edition, 2004, Vol. 43, No.34, pp.4476-4478.
  39. Jiang Biao, Jia Jia Dong, Yu Gui Si, Xiao Long Zhao, Zuo Gang Huang, Xu Min Advanced Synthesis and Catalysis, 2008, Vol. 350, No.9, pp.1360-1366.
  40. Sukach V. A., Tkachuk V. M., Rusanov E. B., Röschenthaler Gerd-Volker, Vovk M. V. Tetrahedron, 2012, Vol. 68, No.40, pp.8408-8415.
  41. Sukach V. A., Tkachuk V. M., Shoba V. M., Pirozhenko V. V., Rusanov E. B., Chekotilo A. A., Röschenthaler G.-V., Vovk M. V. Eur. J. of Org. Chem., 2014, doi: 10.1002/ejoc.201301542.
  42. McNally Andrew, Evans Brian, Gaunt Matthew J. Angewandte Chemie International Edition, 2006, Vol. 45, No.13, pp.2116-2119.
  43. Thayumanavan Rajeswari, Dhevalapally Buchiramachary, Sakthivel Kandasamy, Tanaka Fujie, Barbas Carlos F. Tetrahedron Lett., 2002, Vol. 43, No.21, pp.3817-3820.
  44. Sunden Henrik, Rios Ramon, Xu Yongmei, Eriksson Lars, Cordova Armando, Advanced Synthesis and Catalysis, 2007, Vol. 349, No.17, pp.2549-2555.
  45. Ramachary, Dhevalapally B., Sakthidevi Rajasekar Organic and Biomolecular Chem., 2008, Vol. 6, No.14, pp.2488-2492.
  46. Asami Masatoshi Tetrahedron Lett., 1985, Vol. 26, No.47, pp.5803-5806.
  47. Asami Masatoshi, Ishizaki Tatsuya, Inoue Seiichi Tetrahedron: Asymmetry, 1994, Vol. 5, No.5, pp.793-796.
  48. Masatoshi Asami, Takashi Suga, Kiyoshi Honda, Seiichi Irroue Tetrahedron Lett., 1997, Vol. 38, No.36, pp.6425-6428.

Published

2014-03-06

How to Cite

(1)
Tkachuk, V. M.; Shoba, V. M.; Sukach, V. A.; Vovk, M. V. (S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine – an Effective Catalyst of Asymmetric Synthesis. J. Org. Pharm. Chem. 2014, 12, 3-16.

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Section

Original Researches