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Peptide-catalyzed stereoselective Michael addition of aldehydes and ketones to heterocyclic nitroalkenes

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Abstract

Stereoselective Michael addition of enolizable carbonyl compounds to a furane-derived nitroalkene was catalyzed by di- and tripeptide organocatalysts. The most competent catalysts were tripeptides possessing Pro–Pro–Glu structure. With aldehydes, Michael adducts were obtained in high yields and with medium-to-high diastereo- (up to 13:1 d.r.) and enantiomeric purities (up to 99% ee). The reaction was less stereoselective with cyclic ketones than with aldehydes.

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References

  1. Joule JA, Mills K (2010) Heterocyclic chemistry, 5th edn. Wiley-Blackwell, Chichester

    Google Scholar 

  2. Corey EJ, Czakó B, Kürti L (2007) Molecules and medicine. Wiley, Hoboken

    Google Scholar 

  3. Albrecht L, Ransborg LK, Jørgensen KA (2012) Catal Sci Technol 2:1089

    Article  CAS  Google Scholar 

  4. Vetica F, Chauhan P, Dochain S, Enders D (2017) Chem Soc Rev 46:1661

    Article  CAS  Google Scholar 

  5. Sethuraman I, Jose CM, Subbu P (2013) Curr Org Chem 17:2038

    Article  Google Scholar 

  6. Zhang Y, Wang W (2012) Catal Sci Technol 2:42

    Article  CAS  Google Scholar 

  7. Vicario JL, Badia D, Carrillo L (2007) Synthesis 2007:2065

  8. Tsogoeva SB (2007) Eur J Org Chem 2007:1701

  9. Miller SJ (2004) Acc Chem Res 37:601

    Article  CAS  Google Scholar 

  10. Davie EAC, Mennen SM, Xu Y, Miller SJ (2007) Chem Rev 107:5759

    Article  Google Scholar 

  11. Wennemers H (2011) Chem Commun 47:12036

    Article  CAS  Google Scholar 

  12. Lewandowski B, Wennemers H (2014) Curr Opin Chem Biol 22:40

    Article  CAS  Google Scholar 

  13. Shugrue CR, Miller SJ (2017) Chem Rev 117:11894

    Article  CAS  Google Scholar 

  14. Miller SJ, Copeland GT, Papaioannou N, Horstmann TE, Ruel EM (1998) J Am Chem Soc 120:1629

    Article  CAS  Google Scholar 

  15. Jordan PA, Kayser-Bricker KJ, Miller SJ (2010) Proc Natl Acad Sci USA 107:20620

    Article  CAS  Google Scholar 

  16. Han S, Miller SJ (2013) J Am Chem Soc 135:12414

    Article  CAS  Google Scholar 

  17. Fiori KW, Puchlopek ALA, Miller SJ (2009) Nat Chem 1:630

    Article  CAS  Google Scholar 

  18. Krattiger P, Kovasy R, Revell JD, Ivan S, Wennemers H (2005) Org Lett 7:1101

    Article  CAS  Google Scholar 

  19. Córdova A, Zou W, Dziedzic P, Ibrahem I, Reyes E, Xu Y (2006) Chem Eur J 12:5383

    Article  Google Scholar 

  20. Dziedzic P, Zou W, Hafren J, Cordova A (2006) Org Biomol Chem 4:38

    Article  CAS  Google Scholar 

  21. Revell JD, Wennemers H (2008) Adv Synth Catal 350:1046

    Article  CAS  Google Scholar 

  22. Yan J, Wang L (2009) Chirality 21:413

    Article  CAS  Google Scholar 

  23. Bayat S, Tejo BA, Salleh AB, Abdmalek E, Normi YM, Rahman MBA (2013) Chirality 25:726

    Article  CAS  Google Scholar 

  24. Psarra A, Kokotos CG, Moutevelis-Minakakis P (2014) Tetrahedron 70:608

    Article  CAS  Google Scholar 

  25. Triandafillidi I, Bisticha A, Voutyritsa E, Galiatsatou G, Kokotos CG (2015) Tetrahedron 71:932

    Article  CAS  Google Scholar 

  26. Vega-Peñaloza A, Sánchez-Antonio O, Ávila-Ortiz CG, Escudero-Casao M, Juaristi E (2014) Asian J Org Chem 3:487

    Article  Google Scholar 

  27. Bisticha A, Triandafillidi I, Kokotos CG (2015) Tetrahedron Asymmetry 26:102

    Article  CAS  Google Scholar 

  28. Revell JD, Gantenbein D, Krattiger P, Wennemers H (2006) Biopolymers (Pept Sci) 84:105

    Article  CAS  Google Scholar 

  29. Xu Y, Zou W, Sundén H, Ibrahem I, Córdova A (2006) Adv Synth Catal 348:418

    Article  CAS  Google Scholar 

  30. Wiesner M, Revell JD, Wennemers H (2008) Angew Chem Int Ed 47:1871

    Article  CAS  Google Scholar 

  31. Wiesner M, Revell JD, Tonazzi S, Wennemers H (2008) J Am Chem Soc 130:5610

    Article  CAS  Google Scholar 

  32. Wiesner M, Wennemers H (2010) Synthesis 2010:1568

  33. Duschmalé J, Wennemers H (2012) Chem Eur J 18:1111

    Article  Google Scholar 

  34. Bächle F, Duschmalé J, Ebner C, Pfaltz A, Wennemers H (2013) Angew Chem Int Ed 52:12619

    Article  Google Scholar 

  35. Duschmale J, Kohrt S, Wennemers H (2014) Chem Commun 50:8109

    Article  CAS  Google Scholar 

  36. Kastl R, Wennemers H (2013) Angew Chem Int Ed 52:7228

    Article  CAS  Google Scholar 

  37. Arakawa Y, Wiesner M, Wennemers H (2011) Adv Synth Catal 353:1201

    Article  CAS  Google Scholar 

  38. Arakawa Y, Wennemers H (2013) Chemsuschem 6:242

    Article  CAS  Google Scholar 

  39. Grünenfelder CE, Kisunzu JK, Wennemers H (2016) Angew Chem Int Ed 55:8571

    Article  Google Scholar 

  40. Akagawa K, Satou J, Kudo K (2016) J Org Chem 81:9396

    Article  CAS  Google Scholar 

  41. Akagawa K, Iwasaki Y, Kudo K (2016) Eur J Org Chem 2016:4460

  42. Durini M, Sahr FA, Kuhn M, Civera M, Gennari C, Piarulli U (2011) Eur J Org Chem 2011:5599

  43. Borges-González J, Feher-Voelger A, Crisóstomo FP, Morales EQ, Martín T (2017) Adv Synth Catal 359:576

    Article  Google Scholar 

  44. Cao D, Fang G, Zhang J, Wang H, Zheng C, Zhao G (2016) J Org Chem 81:9973

    Article  CAS  Google Scholar 

  45. Akagawa K, Kudo K (2017) Acc Chem Res 50:2429

    Article  CAS  Google Scholar 

  46. Metrano AJ, Abascal NC, Mercado BQ, Paulson EK, Hurtley AE, Miller SJ (2017) J Am Chem Soc 139:492

    Article  CAS  Google Scholar 

  47. Gao S, Tu YQ, Hu X, Wang S, Hua R, Jiang Y, Zhao Y, Fan X, Zhang S (2006) Org Lett 8:2373

    Article  CAS  Google Scholar 

  48. Pansare SV, Pandya K (2006) J Am Chem Soc 128:9624

    Article  CAS  Google Scholar 

  49. Benoiton NL (2006) Chemistry of peptide synthesis. Taylor & Francis, Boca Raton

    Google Scholar 

  50. Lu D, Gong Y, Wang W (2010) Adv Synth Catal 352:644

    Article  CAS  Google Scholar 

  51. Chen F, Huang S, Zhang H, Liu F, Peng Y (2008) Tetrahedron 64:9585

    Article  CAS  Google Scholar 

  52. Hernández JG, García-López V, Juaristi E (2012) Tetrahedron 68:92

    Article  Google Scholar 

  53. de Boer JW, Browne WR, Harutyunyan SR, Bini L, Tiemersma-Wegman TD, Alsters PL, Hage R, Feringa BL (2008) Chem Commun:3747

  54. Tsunematsu H, Isobe R, Hanazono H, Soeda Y, Inagaki M, Ito N, Higuchi R, Yamamoto M (1999) Chem Pharm Bull 47:1040

    Article  CAS  Google Scholar 

  55. Hiroshi F, Hidenori K, Norio I, Ichizo M, Hideo O (1983) Bull Chem Soc Jpn 56:766

    Article  Google Scholar 

  56. Zhang A, Guo Y (2008) Chem Eur J 14:8939

    Article  CAS  Google Scholar 

  57. Yu H, Liu M, Han S (2014) Tetrahedron 70:8380

    Article  CAS  Google Scholar 

  58. Wang Y, Lin J, Wei K (2014) Tetrahedron Asymmetry 25:1599

    Article  CAS  Google Scholar 

  59. Zheng Z, Perkins BL, Ni B (2010) J Am Chem Soc 132:50

    Article  CAS  Google Scholar 

  60. Nugent TC, Bibi A, Sadiq A, Shoaib M, Umar MN, Tehrani FN (2012) Org Biomol Chem 10:9287

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the Slovak Research and Development Agency under the contract no. APVV-15-0039.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, 842 15, Bratislava, Slovakia

    Viera Poláčková, Patrícia Čmelová & Radovan Šebesta

  2. Institute of Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, 842 15, Bratislava, Slovakia

    Renáta Górová

Authors
  1. Viera Poláčková
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  2. Patrícia Čmelová
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  3. Renáta Górová
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  4. Radovan Šebesta
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Corresponding author

Correspondence to Radovan Šebesta.

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Poláčková, V., Čmelová, P., Górová, R. et al. Peptide-catalyzed stereoselective Michael addition of aldehydes and ketones to heterocyclic nitroalkenes. Monatsh Chem 149, 729–736 (2018). https://doi.org/10.1007/s00706-017-2126-2

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  • DOI: https://doi.org/10.1007/s00706-017-2126-2

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