Direct catalytic enantioselective mannich reactions: Synthesis of protected anti-α,β-diamino acids

Journal of the American Chemical Society

Volumn 129, Issue 35, 2007, Pages 10632-10633

  Cutting, Gary A ^a   Stainforth, Nikki E ^b   John, Matthew P ^c   Kociok Köhn, Gabriele ^a   Willis, Michael C ^b  

^a University of Bath Claverton Down   (United Kingdom)

^b UNIVERSITY OF OXFORD   (United Kingdom)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; ALPHA,BETA DIAMINO ACID; BETA AMINO ACID; DIAMINE; ESTER; IMIDE; IMINE; UNCLASSIFIED DRUG; DIAMINO ACID;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MANNICH REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; CHEMISTRY; STEREOISOMERISM;

AMINO ACIDS, DIAMINO; CATALYSIS; STEREOISOMERISM;

EID: 34848910488     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja073473f     Document Type: Article

References (46)

1. Viso, A.; Fernández de la Pradilla, R.; García, A.; Flores, A. Chem. Rev. 2005, 105, 3167.
2. For a review on the chemistry of vicinal diamines, see; Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580.
3. (a) Chowdari, N. S.; Ahmad, M.; Albertshofer, K.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2006, 8, 2839.
4. (b) Okada, A.; Shibuguchi, T.; Ohshima, T.; Masu, H.; Yamaguchi, K.; Shibasaki, M. Angew. Chem., Int. Ed. 2005, 44, 4564.
5. (c) Ooi, T.; Kameda, M.; Fujii, J.-i; Maruoka, K. Org. Lett. 2004, 6, 2397.
6. (d) Benardi, L.; Gothelf, A. S.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2003, 68, 2583.
7. Selected examples: (a) Suto, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 500.
8. (b) Saruhasi, K.; Kobayahi, S. J. Am. Chem. Soc. 2006, 128, 11232.
9. (c) Ihori, Y.; Yamashita, Y.; Ishitani, H.; Kobayahi, S. J. Am. Chem. Soc. 2005, 127, 15528.
10. (d) Kobayashi, S.; Matsubara, R.; Nakamura, Y.; Kitagawa, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 2507.
11. (e) Akiyama, T.; Saitoh, Y.; Morita, H.; Fuchibe, K. Adv. Synth. Catal. 2005, 347, 1523.
12. (f) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Ind. Ed. 2004, 43, 1566.
13. (g) Josephsohn, N. S.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 3734.
14. (h) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964.
15. (i) Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drury, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67.
16. Selected examples: (a) Guo, Q.-X.; Liu, H.; Guo, C.; Luo, S.-W.; Gu, Y.; Gong, L.-Z. J. Am. Chem. Soc. 2007, 129, 3790.
17. (b) Cheong, P. H.-Y.; Zhang, H.; Thayumanavan, R.; Tanaka, F.; Houk, K. N.; Barbas, C. F., III. Org. Lett. 2006, 8, 811.
18. (c) Yamaguchi, A.; Matsunaga, S.; Shibasaki, M. Tetrahedron Lett. 2006, 47, 3985.
19. (d) Sugita, M.; Yamaguchi, A.; Yamigiwa, N.; Handa, S.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2005, 7, 5339.
20. (e) Ting, A.; Lou, S.; Schaus, S. E. Org. Lett. 2006, 8, 2003.
21. (f) Lou, S.; Taoka, B. M.; Ting, A.; Schaus, S. E. J. Am. Chem. Soc. 2005, 127, 11256.
22. (g) Hayashi, Y.; Urushima, T.; Shoji, M.; Uchimaru, T.; Shiina, I. Adv. Synth. Catal. 2005, 347, 1595.
23. (h) Cobb, A. J. A.; Shaw, D. M.; Longbottom, D. A.; Gold, J. B.; Ley, S. V. Org. Biomol. Chem. 2005, 3, 84.
24. (i) Hamashima, Y.; Sasamoto, N.; Hotta, D.; Somei, H.; Umebayashi, N.; Sodeoka, M. Angew. Chem., Int. Ed. 2005, 44, 1525.
25. (j) Zhuang, W.; Saaby, S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 4476.
26. (k) Marigo, M.; Juhl, K.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1367.
27. (l) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338.
28. (a) Zhang, H.; Mifsud, M.; Tanaka, F.; Barbas, C. F., III. J. Am. Chem. Soc. 2006, 128, 9630.
29. (b) Mitsumori, S.; Zhang, H.; Cheong, P. H.-Y.; Houk, K. N.; Tanaka, F.; Barbas, C. F., III. J. Am. Chem. Soc., 2006, 128, 1040.
30. (c) Ibrahem, I.; Córdova, A. Chem. Commun. 2006, 1760.
31. For examples of anti-selective Mannich reactions employing hydroxyl-substituted ketones, see: (a) Trost, B. M.; Jaratjaroonphong, J.; Reutrakul, V. J. Am. Chem. Soc. 2006, 128, 2778.
32. (b) Matsunaga, S.; Kumagai, N.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
33. (a) Harada, S.; Handa, S.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2005, 44, 4365.
34. (b) Also see ref 3d.
35. (a) Willis, M. C.; Cutting, G. A.; Piccio, V. J.-D.; Durbin, M. J.; John, M. P. Angew. Chem., Int. Ed. 2005, 44, 1543.
36. (b) Willis, M. C.; Piccio, V. J.-D. Synlett 2002, 1625.
37. For examples of the use of a chiral version of 1 in diastereoselective aldol additions, see: (a) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757.
38. (b) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1987, 109, 7151.
39. (c) Lago, M. A.; Samanen, J.; Elliot, J. D. J. Org. Chem. 1992, 57, 3493.
40. (d) Boger, D. L.; Colletti, S. L.; Honda, T.; Menezes, R. F. J. Am. Chem. Soc. 1994, 116, 5607.
41. McManus, H. A.; Guiry, P. J. Chem. Rev. 2004, 104, 4151.
42. (a) Kanemasa, S.; Oderaotoshi, Y.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Org. Chem. 1997, 62, 6454.
43. (b) Iserloh, U.; Oderaotoshi, Y.; Kanemasa, S.; Curran, D. P. Org. Synth. 2003, 80, 46.
44. (a) Fueloep, F.; Martinek, T. A.; Toth, G. K. Chem. Soc. Rev. 2006, 35, 323.
45. (b) Sewald, N. Angew. Chem. Int. Ed. 2003, 42, 5794.
46. For a review of enantioselective additions to imines, see: Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.