Peptide-catalyzed 1,4-addition reactions of aldehydes to nitroolefins

Chimia

Volumn 67, Issue 4, 2013, Pages 279-282

  Kastl, Robert ^a   Arakawa, Yukihiro ^a   Duschmalé, JÖrg ^a   Wiesner, Markus ^a   Wennemers, Helma ^a  

^a Institute of Neuroinformatics Zurich   (Switzerland)

Author keywords

Asymmetric catalysis; Conjugate addition reaction; Nitroolefins; Organocatalysis; Peptides

Indexed keywords

EID: 84877743533     PISSN: 00094293     EISSN: None     Source Type: Journal    
DOI: 10.2533/chimia.2013.279     Document Type: Article

References (40)

1. J. Vicario, 'Organocatalytic Enantioselective Conjugate Addition Reactions: A Powerful Tool for the Stereocontrolled Synthesis of Complex Molecules', RSC, Cambridge, 2010.
2. For recent reviews, see: D. Roca-Lopez, D. Sadaba, I. Delso, R. P. Herrera, T. Tejero, P. Merino, Tetrahedron: Asymm. 2010, 21, 2561
3. S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471.
4. For selected examples, see: a) J. M. Betancort, C. F. Barbas III, Org. Lett. 2001, 3, 3737
5. A. Alexakis, O. Andrey, Org. Lett. 2002, 4, 3611
6. O. Andrey, A. Alexakis, A. Tomassini, G. Bernardinelli, Adv. Synth. Catal. 2004, 346, 1147
7. Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. Int. Ed. 2005, 44, 4212
8. W. Wang, J. Wang, H. Li, Angew. Chem. Int. Ed. 2005, 44, 1369
9. C. Palomo, S. Vera, A. Mielgo, E. Gómez-Bengoa, Angew. Chem. Int. Ed. 2006, 45, 5984
10. H. Uehara, C. F. Barbas III, Angew. Chem. Int. Ed. 2009, 48, 9848
11. Y.-F. Ting, C. Chang, R. J. Reddy, D. R. Magar, K. Chen, Chem. Eur. J. 2010, 16, 7030
12. H. Rahaman, Á Madarász, I. Pápai, P. M. Pihko, Angew. Chem. Int. Ed. 2011, 50, 6123.
13. P. Krattiger, C. McCarthy, A. Pfaltz, H. Wennemers, Angew. Chem. Int. Ed. 2003, 42, 1722.
14. H. Wennemers, J. Pept. Sci. 2012, 18, 437.
15. P. Krattiger, R. Kovasy, J. D. Revell, S. Ivan, H. Wennemers, Org. Lett. 2005, 7, 1101
16. P. Krattiger, R. Kovasy, J. D. Revell, H. Wennemers, QSAR Comb. Sci. 2005, 24, 1158.
17. J. D. Revell, D. Gantenbein, P. Krattiger, H. Wennemers, Biopolymers 2006, 84, 105
18. J. D. Revell, H. Wennemers, Tetrahedron 2007, 63, 8420
19. J. D. Revell, H. Wennemers, Adv. Synth. Catal. 2008, 350, 1046
20. M. Messerer, H. Wennemers, Synlett 2011, 499.
21. M. Wiesner, J. D. Revell, S. Tonazzi, H. Wennemers, J. Am. Chem. Soc. 2008, 130, 5610.
22. M. Wiesner, J. D. Revell, H. Wennemers, Angew. Chem. Int. Ed. 2008, 47, 1871.
23. M. Wiesner, M. Neuburger, H. Wennemers, Chem. Eur. J. 2009, 15, 10103.
24. M. Wiesner, G. Upert, G. Angelici, H. Wennemers, J. Am. Chem. Soc. 2010, 132, 6.
25. M. Wiesner, H. Wennemers, Synthesis 2010, 1568.
26. Y. Arakawa, M. Wiesner, H. Wennemers, Adv. Synth. Catal. 2011, 353, 1201.
27. Y. Arakawa, H. Wennemers, ChemSusChem 2013, 6, 242.
28. J. Duschmalé, H. Wennemers, Chem. Eur. J. 2012, 18, 1111.
29. J. Duschmalé, J. Wiest, M. Wiesner, H. Wennemers, Chem. Sci. 2013, 4, 1312.
30. 'Handbook of Asymmetric Heterogeneous Catalysis', Eds. K. Ding, Y. Uozumi, Wiley- VCH, Weinheim, 2008.
31. For recent examples of immobilized chiral amine-based organocatalysts, see: a) L. Tuchman-Shukron, S. J. Miller, M. Portnoy, Chem. Eur. J. 2012, 18, 2290
32. C. Ayats, A. H. Henseler, M. A. Pericàs, ChemSusChem 2012, 5, 320
33. E. Alza, S. Sayalero, P. Kasaplar, D. Almaşi, M. A. Pericàs, Chem. Eur. J. 2011, 17, 11585
34. M. Gruttadauria, A. M. P. Salvo, F. Giacalone, P. Agrigento, R. Noto, Eur. J. Org. Chem. 2009, 5437.
35. For a review, see: K. Gajcy, S. Lochynski, T. Librowski, Curr. Med. Chem. 2010, 17, 2338.
36. D. Seebach, M. Brenner, M. Rueping, B. Schweizer, B. Jaun, Chem. Commun. 2001, 207
37. D. Seebach, M. Brenner, M. Rueping, B. Jaun, Chem. Eur. J. 2002, 8, 573
38. D. Seebach, D. F. Hook, A. Glättli, Biopolymers 2006, 84, 23
39. P. G. Vasudev, S. Chatterjee, N. Shamala, P. Balaram, Chem. Rev. 2011, 111, 657
40. S. H. Gellman, Acc. Chem. Res. 1998, 31, 173.