A novel design of roof-shaped anthracene-fused chiral prolines as organocatalysts for asymmetric Mannich reactions

Tetrahedron Asymmetry

Volumn 17, Issue 21, 2006, Pages 2963-2969

  Sasaoka, Aika ^a   Uddin, Md Imam ^a   Shimomoto, Ai ^a   Ichikawa, Yoshiyasu ^a   Shiro, Motoo ^b   Kotsuki, Hiyoshizo ^a  

^a KOCHI UNIVERSITY   (Japan)

^b RIGAKU CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINE; AMINO ACID; ANTHRACENE; ESTER; KETONE; MALEIC ANHYDRIDE; MENTHOL; PROLINE;

ARTICLE; CARBOXYLATION; CATALYST; CHIRALITY; DIASTEREOISOMER; DIELS ALDER REACTION; LITHIATION; MANNICH REACTION; PRIORITY JOURNAL; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 33845209565     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.11.010     Document Type: Article

References (38)

1. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 40 (2001) 3726-3748
2. Dalko P.I., and Moisan L. Angew. Chem., Int. Ed. 43 (2004) 5138-5175
3. In: Houk K.N., and List B. (Eds). Acc. Chem. Res. 37 (2004)
4. In: List B., and Bolm C. (Eds). Adv. Synth. Catal. 346 (2004)
5. In: Berkessel A., and Gröger H. (Eds). Asymmetric Organocatalysis (2005), Wiley-VCH, Weinheim
6. In: Kocovosky P., and Malkov A.V. (Eds). Tetrahedron 62 (2006)
7. List B., Lerner R.A., and Barbas III C.F. J. Am. Chem. Soc. 122 (2000) 2395-2396
8. Reviews:. List B. Synlett 11 (2001) 1675-1686
9. Gröger H., and Wilken J. Angew. Chem., Int. Ed. 40 (2001) 529-532
10. Palomo C., Oiarbide M., and García J.M. Chem. Eur. J. 8 (2002) 37-44
11. Jarvo E.R., and Miller S.J. Tetrahedron 58 (2002) 2481-2495
12. List B. Tetrahedron 58 (2002) 5573-5590
13. For example, see:. Terakado D., Takano M., and Oriyama T. Chem. Lett. 34 (2005) 962-963
14. Kano T., Takai J., Tokuda O., and Maruoka K. Angew. Chem., Int. Ed. 44 (2005) 3055-3057
15. Kano T., Yamaguchi Y., Tokuda O., and Maruoka K. J. Am. Chem. Soc. 127 (2005) 16408-16409
16. Cheong P.H.-Y., Zhang H., Thayumanavan R., Tanaka F., Houk K.N., and Barbas III C.F. Org. Lett. 8 (2006) 811-814
17. Mitsumori S., Zhang H., Cheong P.H.-Y., Houk K.N., Tanaka F., and Barbas III C.F. J. Am. Chem. Soc. 128 (2006) 1040-1041
18. Kano T., Tokuda O., and Maruoka K. Tetrahedron Lett. 47 (2006) 7423-7426
19. Sekiguchi Y., Sasaoka A., Shimomoto A., Fujioka S., and Kotsuki H. Synlett (2003) 1655-1658
20. Ishii T., Fujioka S., Sekiguchi Y., and Kotsuki H. J. Am. Chem. Soc. 126 (2004) 9558-9559
21. Ikishima H., Sekiguchi Y., Ichikawa Y., and Kotsuki H. Tetrahedron 62 (2006) 311-316
22. Atherton J.C.C., and Jones S. Tetrahedron 59 (2003) 9039-9057
23. Reviews:. Trost B.M., and Crawley M.L. Chem. Rev. 103 (2003) 2921-2943
24. Matsunaga H., Ishizuka H., and Kunieda T. Tetrahedron 61 (2005) 8073-8094
25. See also:. Sarotti A.M., Spanevello R.A., and Suárez A.G. Tetrahedron Lett. 45 (2004) 8203-8206
26. Sarotti A.M., Spanevello R.A., and Suárez A.G. Org. Lett. 8 (2006) 1487-1490
27. For reviews of proline-catalyzed asymmetric Mannich reactions, see:. Córdova A. Acc. Chem. Res. 37 (2004) 102-112
28. Notz W., Tanaka F., and Barbas III C.F. Acc. Chem. Res. 37 (2004) 580-591
29. Marques M.M.B. Angew. Chem., Int. Ed. 45 (2006) 348-352
30. Yates P., and Eaton P. J. Am. Chem. Soc. 82 (1960) 4436-4437
31. See also:. Kloetzel M.C. Org. React. 4 (1948) 1-59
32. Reviews:. Beak P., Zajdel W.J., and Reitz D.B. Chem. Rev. 84 (1984) 471-523
33. Beak P., Basu A., Gallagher D.J., Park Y.S., and Thayumanavan S. Acc. Chem. Res. 29 (1996) 552-560
34. Stürmer R., Schäfer B., Wolfart V., Stahr H., Kazmaier U., and Helmchen G. Synthesis (2001) 46-48
35. List B. J. Am. Chem. Soc. 122 (2000) 9336-9337
36. List B., Pojarliev P., Biller W.T., and Martin H.J. J. Am. Chem. Soc. 124 (2002) 827-833
37. Hayashi Y., Tsuboi W., Shoji M., and Suzuki N. J. Am. Chem. Soc. 125 (2003) 11208-11209
38. Notz W., Watanabe S., Chowdari N.S., Zhong G., Betancort J.M., Tanaka F., and Barbas III C.F. Adv. Synth. Catal. 346 (2004) 1131-1140