Clarification of the role of water in proline-mediated aldol reactions

Journal of the American Chemical Society

Volumn 129, Issue 49, 2007, Pages 15100-15101

  Zotova, Natalia ^a   Franzke, Axel ^a   Armstrong, Alan ^a   Blackmond, Donna G ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; PROLINE; WATER;

ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROLYSIS; KINETICS; STOICHIOMETRY;

ALCOHOLS; ALDEHYDES; CATALYSIS; KINETICS; PROLINE; WATER;

EID: 37049010984     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0738881     Document Type: Article

References (22)

1. List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395.
2. Seayad, J.; List, B. Org. Biomol. Chem. 2005, 3, 719.
3. (a) Bahmanyar, S.; Houk, K. N.; Martin, H. J.; List, B. J. Am. Chem. Soc. 2003, 125, 2475.
4. (b) Hoang, L.; Bahmanyar, S.; Houk, K. N.; List, B. J. Am. Chem. Soc. 2003, 125, 16.
5. (c) Clemente, F. R.; Houk, K. N. Angew. Chem., Int. Ed. 2004, 116, 5890.
6. (a) Hartikka, A.; Arvidsson, P. M. Tetrahedron: Asymmetry 2004, 15, 1831.
7. (b) Nyberg, A. I.; Usano, A.; Pihko, P. M. Synlett 2004, 11, 1891.
8. (c) Pihko, P. M.; Laurikainen, K. M.; Usano, A.; Nyberg A.; Kaavi, J. A. Tetrahedron 2006, 62, 317.
9. (d) Mathew, S. P.; Klussmann, M.; Iwamura, H.; Wells, D. H., Jr.; Armstrong, A.; Blackmond, D. G. Chem. Commun. 2006, 41, 4291.
10. (a) Blackmond, D. G.; Armstrong, A.; Coombe, V.; Wells, A. Angew. Chem., Int. Ed. 2007, 46, 3798.
11. (b) Brogan, A. P.; Dickerson, T. J.; Janda, K. D. Angew. Chem., Int. Ed. 2006, 45, 8100.
12. Seebach, D.; Beck, A. K.; Badine, D. M.; Limbach, M.; Eschenmoser, A.; Treasurywala, A. M.; Hobi, R.; Prikoszovich, W.; Linder, B. Helv. Chim. Acta 2007, 90, 425.
13. (a) Mathew, J. S.; Klussmann, M.; Iwamura, H.; Valera, F.; Futran, A.; Emanuelsson, E. A. C.; Blackmond, D. G. J. Org. Chem. 2006, 71, 4711.
14. (b) Blackmond, D. G. Angew. Chem., Int. Ed. 2005, 44, 4302.
15. 2O cases exhibited ≤10 % conversion in ≥6 days. A significant influence of water on ee or de in less sluggish, clean reactions has not been clearly shown.
16. Seebach, D.; Boes, M.; Naef, R.; Schweizer, W. B. J. Am. Chem. Soc. 1983, 105, 5390.
17. Orsini, F.; Pelizzoni, F.; Forte, M.; Destro, R.; Gariboldi, P. Tetrahedron 1988, 44, 519.
18. (a) Kano, T.; Takai, J.; Tokuda, O.; Maruoka, K. Angew. Chem., Int. Ed. 2005, 44, 3055.
19. (b) Dambruoso, P.; Massi, A.; Dondoni, A. Org. Lett. 2005, 9, 4657.
20. Grigg, R. E.; Sarker, M. A. B. Tetrahedron 2006, 10332.
21. Marquez, C.; Metzger, J. O. Chem. Commun. 2006, 1539.
22. 2O even when this step is rate-limiting. Scheme 1 does not account for this possibility, and it is not consistent with our results for aromatic aldehydes.