Influence of the organocatalyst in the aldol/Mannich-type product selectivities in C-C bond forming reactions

ACS Catalysis

Volumn 1, Issue 2, 2011, Pages 70-75

  Domínguez De María, Pablo ^a   Bracco, Paula ^a   Castelhano, Luiz Fernando ^a   Bargeman, Gerrald ^a  

^a AKZO NOBEL CENTRAL RESEARCH   (Netherlands)

Author keywords

aldol; mannich; organocatalysis; oxazolidinone; Proline; pyrrolidine

Indexed keywords

ALDOL; MANNICH; ORGANOCATALYSIS; OXAZOLIDINONES; PROLINE; PYRROLIDINES;

ACETONE; ALDEHYDES; CATALYSIS; CONDENSATION; CONDENSATION REACTIONS; ESTERS; RATE CONSTANTS; REACTION KINETICS;

AMINO ACIDS;

EID: 79952031844     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs100088m     Document Type: Article

References (39)

1. Dondoni, A.; Massi, A. Angew. Chem., Int. Ed. 2008, 47, 4638-4660
2. Melchiorre, P.; Marigo, M.; Carlone, A.; Bartoli, G. Angew. Chem., Int. Ed. 2008, 47, 6138-6171
3. Barbas, C. F., III Angew. Chem., Int. Ed. 2008, 47, 42-47
4. List, B. Tetrahedron. 2002, 58, 5573-5590
5. Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615-1621
6. Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496-497
7. List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395-2396
8. Zotova, N.; Franzke, A.; Armstrong, A.; Blackmond, D. G. J. Am. Chem. Soc. 2007, 129, 15100-15101
9. Hayashi, Y.; Aratake, S.; Itoh, T.; Okano, T.; Sumiya, T.; Shoji, M. Chem. Commun. 2007, 957-959
10. Marquez, C.; Metzger, J. O. Chem. Commun. 2006, 1539-1541
11. List, B.; Hoang, L.; Martin, H. J. Proc. Natl. Acad. Sci. 2004, 101, 5839-5842
12. Cheong, P.; Houk, K. N. J. Am. Chem. Soc. 2004, 126, 13912-13913
13. Allemann, C.; Gordillo, R.; Clemente, F.; Cheong, P.; Houk, K. N. Acc. Chem. Res. 2004, 37, 558-569
14. Clemente, F.; Houk, K. N. Angew. Chem., Int. Ed. 2004, 43, 5766-5678
15. Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16-17
16. Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475-2479
17. Rankin, K. N.; Gauld, J. W.; Boyd, R. J. J. Phys. Chem. A 2002, 106, 5155-5159
18. Orsini, F.; Pelizzoni, F.; Forte, M.; Sisti, M.; Bombieri, G.; Benetollo, F. J. Heterocycl. Chem. 1989, 26, 837-841
19. Seebach, D.; Boes, M.; Naef, R.; Schweizer, W. B. J. Am. Chem. Soc. 1983, 105, 5390-5398
20. Córdova, A.; Sundén, H.; Xu, Y.; Ibrahem, I.; Zou, W.; Engqvist, M. Chem.-Eur. J. 2006, 12, 5446-5451
21. Isart, C.; Bures, J.; Vilarrasa, J. Tetrahedron Lett. 2008, 49, 5414-5418
22. Seebach, D.; Beck, A. K.; Badine, D. M.; Limbach, M.; Eschenmoser, A.; Treasurywala, A. M.; Hobi, R.; Prikoszvich, W.; Linder, B. Helv. Chim. Acta 2007, 90, 425-471
23. Nozière, B.; Córdova, A. J. Phys. Chem. A 2008, 112, 2827-2837
24. Córdova, A.; Notz, W.; Barbas, C. F., III J. Org. Chem. 2002, 67, 301-303
25. Chi., Y.; Scroggins, S. T.; Boz, E.; Frechet, J. M. J. J. Am. Chem. Soc. 2008, 130, 17287-17289
26. List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573-575
27. Chandrasekhar, S.; Reddy, N. R.; Sultana, S.; Narshihmulu, Ch.; Reddy, K. V. Tetrahedron 2006, 62, 338-345
28. Basu, K.; Richards, J.; Paquette, L. A. Synthesis 2004, 17, 2841-2844
29. Ishikawa, T.; Uedo, E.; Okada, S.; Saito, S. Synlett 1999, 4, 450-452
30. Erkkila, A.; Pihko, P. M. Eur. J. Org. Chem. 2007, 4205-4216
31. Erkkila, A.; Pihko, P. M. J. Org. Chem. 2006, 71, 2538-2541
32. Casas, J.; Sunden, H.; Córdova, A. Tetrahedron Lett. 2004, 45, 6117-6119
33. Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799 Isobutyraldehyde has been reported as a very selective acceptor when cross aldol reactions of aldehydes are intended, which suggests that isobutyraldehyde-enamine is non-reactive
34. Diner, P.; Kjaersgaard, A.; Lie, M. A.; Jorgensen, K. A. Chem.-Eur. J. 2008, 14, 122-127
35. Palomo, C.; Mielgo, A. Angew. Chem., Int. Ed. 2006, 45, 7876-7880
36. Franzen, J.; Marigo, M.; Fielenbach, D.; Wabnitz, T. C.; Kjaersgaard, A.; Jorgensen, K. A. J. Am. Chem. Soc. 2005, 127, 18296-18304
37. Betancort, J. M.; Barbas, C. F., III Org. Lett. 2001, 3, 3737-3740
38. Zhang, F.; Peng, Y.; Liao, S.; Gong, Y. Tetrahedron. 2007, 63, 4636-4641
39. Funabiki, K.; Yamamoto, H.; Nagaya, H.; Matsui, M. Tetrahedron Lett. 2006, 47, 5507-5510