Enantioselective Mannich-type reaction catalyzed by a chiral phosphoric acid bearing an (S)-biphenol backbone

Synlett

Volumn , Issue 10, 2009, Pages 1664-1666

  Akiyama, Takahiko ^a   Katoh, Takuya ^a   Mori, Keiji ^a   Kanno, Kazuaki ^b  

^a GAKUSHUIN UNIVERSITY   (Japan)

^b MITSUBISHI CHEMICAL CORPORATION   (Japan)

Author keywords

Asymmetric synthesis; Biphenol; Chiral Br nsted acid; Mannich type reaction; Phosphoric acid

Indexed keywords

ACETAL DERIVATIVE; ALDIMINE; BENZALDEHYDE; BIPHENYL DERIVATIVE; BRONSTED ACID; CINNAMALDEHYDE; KETENE DERIVATIVE; KETENE SILYL ACETAL; LEWIS ACID; PHOSPHORIC ACID; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; DEALKYLATION; ENANTIOSELECTIVITY; HYDROGEN BOND; MANNICH REACTION;

EID: 67649383139     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217330     Document Type: Article

References (51)

1. Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999.
2. (a) Asymmetric Organocatalysis; Berkessel, A.; Gröger, H., Eds.; Wiley-VCH: Weinheim, 2005.
3. (b) Enantioselective Organocatalysis; Dalko, P. I., Ed.; Wiley-VCH: Weinheim, 2007.
4. (a) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem. Int. Ed. 2004, 43, 1566.
5. (b) Itoh, J.; Fuchibe, K.; Akiyama, T. Synthesis 2008, 1319.
6. For reviews of Mannich reactions, see: (a) Friestad, G. K.; Mathiesa, A. K. Tetrahedron 2007, 63, 2541.
7. (b) Ting, A.; Schaus, S. E. Eur. J. Org. Chem. 2007, 5797.
8. Yamanaka, M.; Itoh, J.; Fuchibe, K.; Akiyama, T. J. Am. Chem. Soc. 2007, 129, 6756.
9. For selected examples, see: (a) Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356.
10. (b) Uraguchi, D.; Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2004, 126, 11804.
11. (c) Uraguchi, D.; Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2005, 127, 9360.
12. (d) Rowland, G. B.; Zhang, H.; Rowland, E. B.; Chennamadhavuni, S.; Wang, Y.; Antilla, J. C. J. Am. Chem. Soc. 2005, 127, 15696.
13. (e) Hoffmann, S.; Seayad, A. M.; List, B. Angew. Chem. Int. Ed. 2005, 44, 7424.
14. (f) Terada, M.; Machioka, K.; Sorimachi, K. Angew. Chem. Int. Ed. 2006, 45, 2254.
15. (g) Storer, R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84.
16. (h) Seayad, J.; Seayad, A. M.; List, B. J. Am. Chem. Soc. 2006, 128, 1086.
17. (i) Chen, X.-H.; Xu, X.-Y.; Liu, H.; Cun, L.-F.; Gong, L.-Z. J. Am. Chem. Soc. 2006, 128, 14802.
18. (j) Terada, M.; Sorimachi, K. J. Am. Chem. Soc. 2007, 129, 292.
19. (k) Kang, Q.; Zhao, Z.-A.; You, S.-L. J. Am. Chem. Soc. 2007, 129, 1484.
20. (l) Guo, Q.-X.; Liu, H.; Guo, C.; Luo, S.-W.; Gu, Y.; Gong, L.-Z. J. Am. Chem. Soc. 2007, 129, 3790.
21. (m) Jia, Y.-X.; Zhong, J.; Zhu, S.-F.; Zhang, C.-M.; Zhou, Q.-L. Angew. Chem. Int. Ed. 2007, 46, 5565.
22. (n) Rueping, M.; Sugiono, E.; Schoepke, F. R. Synlett 2007, 1441.
23. (o) Rueping, M.; Sugiono, E.; Theissmann, T.; Kuenkel, A.; Koeckritz, A.; Pews-Davtyan, A.; Nemati, N.; Beller, M. Org. Lett. 2007, 9, 1065.
24. (p) Rueping, M.; Theissmann, T.; Kuenkel, A.; Koenigs, R. M. Angew. Chem. Int. Ed. 2008, 47, 6798.
25. (q) Terada, M.; Tanaka, H.; Sorimachi, K. Synlett 2008, 1661.
26. (r) Xu, S.; Wang, Z.; Zhang, X.; Zhang, X.; Ding, K. Angew. Chem. Int. Ed. 2008, 47, 2840.
27. (s) Terada, M.; Soga, K.; Momiyama, N. Angew. Chem. Int. Ed. 2008, 47, 4122.
28. (t) Rueping, M.; Antonchick, A. P. Angew. Chem. Int. Ed. 2008, 47, 5836.
29. For reviews, see: (a) Connon, S. J. Angew. Chem. Int. Ed. 2006, 45, 3909.
30. (b) Akiyama, T.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2006, 348, 999.
31. (c) Akiyama, T. Chem. Rev. 2007, 107, 5744.
32. (d) Akiyama, T. In Acid Catalysis in Modern Organic Synthesis; Yamamoto, H.; Ishihara, K., Eds.; Wiley-VCH: Weinheim, 2008, 62.
33. (e) Terada, M. Chem. Commun. 2008, 4097.
34. For our reports, see: (a) Akiyama, T.; Tamura, Y.; Itoh, J.; Morita, H.; Fuchibe, K. Synlett 2006, 141.
35. (b) Akiyama, T.; Morita, H.; Fuchibe, K. J. Am Chem. Soc. 2006, 128, 13070.
36. (c) Itoh, J.; Fuchibe, K.; Akiyama, T. Angew. Chem. Int. Ed. 2006, 45, 4796.
37. (d) Itoh, J.; Fuchibe, K.; Akiyama, T. Angew. Chem. Int. Ed. 2008, 47, 4016.
38. (e) Akiyama, T.; Honma, Y.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2008, 350, 399.
39. For a chiral phosphoric acid derived from TADDOL, see: Akiyama, T.; Saitoh, Y.; Morita, H.; Fuchibe, K. Adv. Synth. Catal. 2005, 347, 1523.
40. For use of phosphoric acid derived from biphenol derivative, see: (a) Rowland, G. B.; Zhang, H.; Rowland, E. B.; Chennamadhavuni, S.; Wang, Y.; Antilla, J. C. J. Am. Chem. Soc. 2005, 127, 15696.
41. (b) Li, G.; Liang, Y.; Antilla, J. C. J. Am. Chem. Soc. 2007, 129, 5830.
42. (c) Rowland, E. B.; Rowland, G. B.; Rivera-Otero, E.; Antilla, J. C. J. Am. Chem. Soc. 2007, 129, 12084.
43. (d) See also: Moreau, J.; Duboc, A.; Hubert, C.; Hurvois, J.-P.; Renaud, J.-L. Tetrahedron Lett. 2007, 48, 8647.
44. (a) Takai, M.; Urata, T.; Takahashi, T. JP 2004189696, 2004.
45. See also: (b) Hua, Z.; Vassar, V. C.; Ojima, I. Org. Lett. 2003, 5, 3831.
46. (c) Ojima, I.; Takai, M.; Takahashi, T.; Urata, H. WO 2004076464, 2004.
47. 8P: C, 60.24; H, 3.69; N, 5.40. Found: C, 60.13; H, 3.66; N, 5.45%.
48. 3): δ = 177.7, 144.3, 139.0, 135.5, 128.3, 127.9, 127.41, 121.0, 117.9, 114.4, 113.9, 64.6, 52.2, 47.4, 24.4, 20.0.
49. When 1a was employed in the reaction with the aldimine derived from benzaldehyde, the corresponding adduct was obtained in 87% ee.3
50. 3
51. For bifunctional Lewis acids, see: Shibasaki, M.; Kanai, M.; Funabashi, K. Chem. Commun. 2002, 1989.