Complete switch of product selectivity in asymmetric direct aldol reaction with two different chiral organocatalysts from a common chiral source

Journal of the American Chemical Society

Volumn 130, Issue 52, 2008, Pages 17666-17667

  Nakayama, Keiji ^a   Maruoka, Keiji ^b  

^a DAIICHI SANKYO CO   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC SYNTHESIS; DIRECT ALDOL REACTION; ORGANOCATALYSTS; PRODUCT SELECTIVITIES;

AMINES;

4 NITROBENZALDEHYDE; BENZALDEHYDE DERIVATIVE; CYCLOHEXANONE; UNCLASSIFIED DRUG;

ALDOL REACTION; ASYMMETRIC SYNTHESIS; CATALYST; CHEMICAL STRUCTURE; CHIRAL ORGANOCATALYST; CHIRALITY; SHORT SURVEY;

EID: 67749137436     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja807807p     Document Type: Short Survey

References (28)

1. Recent reviews (a) Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. ReV. 2007, 107, 5471.
2. (b) Dalko, P. I. EnantioselectiVe Organocatalysis; Wiley-VCH: Weinheim, Germany, 2007.
3. (c) Dondoni, A.; Massi, A. Angew. Chem., Int. Ed. 2008, 47, 2.
4. (a) Poll, T.; Sobczak, A.; Hartmann, H.; Helmchen, G. Tetrahedron Lett. 1985, 26, 3095.
5. (b) Yoshino, T.; Nagata, T.; Haginoya, N.; Yoshikawa, K.; Kanno, H.; Nagamochi, M. PCT Int. Appl. WO2001074774, 2001.
6. Recent reviews (a) Guillena, G.; Najera, C.; Ramon, D. J. Tetrahedron: Asymmetry 2007 , 18, 2249.
7. (b) Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. ReV. 2007,107, 5471.
8. (c) Mlynarski, J.; Paradowska, J. Chem. Soc. ReV. 2008, 37, 1502.
9. Recent selected examples of direct asymmetric aldol reactions: (a) Ramasastry, S. S. V.; Zhang, H.; Tanaka, F.; Barbas, C. F., III J. Am. Chem. Soc. 2007, 129, 288.
10. (b) Luo, S.; Xu, H.; Li, J.; Zhang, L.; Cheng, J.-P. J. Am. Chem. Soc. 2007, 129, 3074.
11. (c) Guizzetti, S.; Benaglia, M.; Raimondi, L.; Celentano, G. Org. Lett. 2007, 9, 1247.
12. (d) Xu, X.-Y.; Wang, Y.-Z; Gong, L.-Z. Org. Lett. 2007, 9, 4247.
13. (e) Liu, J.; Yang, Z.; Wang, Z.; Wang, F.; Chen, X.; Liu, X.; Feng, X.; Su, Z.; Hu, C. J. Am. Chem. Soc. 2008, 130, 5654.
14. (f) Luo, S.; Xu, H.; Zhang, L.; Li, J.; Cheng, J.-P. Org. Lett. 2008, 10, 653.
15. (g) Ramasastry, S. S. V.; Albertshofer, K.; Utsumi, N.; Barbas, C F., III Org. Lett. 2008, 10, 1621.
16. (h) Luo, S.; Xu, H.; Chen, L.; Cheng, J.-P. Org. Lett. 2008, 10, 1775.
17. (i) Hayashi, Y.; Itoh, T.; Aratake, S.; Ishikawa, H. Angew. Chem., Int. Ed. 2008, 47, 2082.
18. (a) Kano, T.; Takai, J.; Tokuda, O.; Maruoka, K. Angew. Chem., Int. Ed. 2005, 44, 3055.
19. (b) Kano, T.; Tokuda, O.; Takai, J.; Maruoka, K. Chem. Asian. J. 2006,1-2, 210.
20. (c) Kano, T.; Yamaguchi, Y.; Tanaka, Y.; Maruoka, K. Angew. Chem., Int. Ed. 2007, 46, 1738.
21. See also: (d) Kano, T.; Tokuda, O.; Maruoka, K. Tetrahedron Lett. 2006, 47, 7423.
22. (a) Kano, T.; Yamaguchi, Y.; Tokuda, O.; Maruoka, K. J. Am. Chem. Soc. 2005, 127, 16408.
23. (b) Kano, T.; Hato, Y.; Maruoka, K. Tetrahedron Lett. 2006, 47, 8467 (see also ref 5c )
24. (a) Brogan, A. P.; Dickerson, T. J.; Janda, K. D. Angew. Chem., Int. Ed. 2006, 45, 8100.
25. (b) Hayashi, Y. Angew. Chem., Int. Ed. 2006, 45, 8103, and references therein.
26. The absolute and relative configuration of the aldol products 5-10 was determined by comparison with the following references (a) Suri, J. T.; Ramachary, D. B.; Barbas, C. F., Jr Org. Lett. 2005, 7, 1383.
27. (b) Gryko, D.; Lipiński, R. Eur. J. Org. Chem. 2006, 3864.
28. (c) Mase, N.; Nakai, Y.; Ohara, N.; Yoda, H.; Takabe, K.; Tanaka, F.; Barbas, C. F., Jr J. Am. Chem. Soc. 2006, 128, 734.