Enantioselectively organocatalytic Michael addition of ketones to alkylidene malonates

Journal of Organic Chemistry

Volumn 72, Issue 11, 2007, Pages 4073-4076

  Cao, Chun Li ^a   Sun, Xiu Li ^a   Zhou, Jiao Long ^a   Tang, Yong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLIDENE MALONATES; MICHAEL ADDITION; ORGANOCATALYSIS;

ADDITION REACTIONS; ENANTIOSELECTIVITY; KETONES; REACTION KINETICS;

CATALYST ACTIVITY;

ALKYL GROUP; KETONE; MALONIC ACID DERIVATIVE; N (PYRROLIDIN 2 YLMETHYL)TRIFLUOROMETHANESULFONAMIDE; SULFONAMIDE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MICHAEL ADDITION; ORGANOCATALYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 34249779259     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070070p     Document Type: Article

References (65)

1. Perlmutter, P. Conjugated Addition Reactions in Organic Synthesis; Pergamon: Oxford, 1992.
2. For recent reviews of asymmetric conjugate addition reactions, see: (a) Tomioka, K.; Nagaoka, Y.; Yamaguchi, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Vol. III, pp 1105-1139.
3. (b) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171.
4. (c) Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877.
5. (d) Christoffers, J.; Baro, A. Angew. Chem., Int. Ed. 2003, 42, 1688.
6. (e) Fagnou, K.; Laurens, M. Chem. Rev. 2003, 103, 169.
7. (f) Ballini, R.; Bosica, G.; Palmieri, A.; Petrini, M. Chem. Rev. 2005, 105, 933.
8. For selected examples for organocatalytically asymmetric addition, see: (a) Brandau, S.; Landa, A.; Franzén, J.; Marigo, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2006, 45, 4305.
9. (b) Chen, Y. K.; Yoshida, M.; Macmillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 9328.
10. (c) Wang, W.; Li, H.; Wang, J.; Zu, L.-S. J. Am. Chem. Soc. 2006, 128, 10354.
11. (d) Wang, J.; Li, H.; Zu, L.-S.; Wei, J.; Xie, H.-X.; Duan, W. H.; Wang, W. J. Am. Chem. Soc. 2006, 128, 12652.
12. (e) Li, H.; Wang, J.; E-Nunu, T.; Zu, L.-S. Jiang, W.; Wei, S.-H.; Wang, W. Chem. Commun. 2007, 878.
13. (a) Hong, B.-C.; Wu, M.-F.; Tseng, H.-C.; Liao, J.-H. Org. Lett. 2006, 8, 2217.
14. (b) Mauro, M.; Bertelsen, S.; Landa, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2006, 128, 5475.
15. (a) Melchiorre, P.; Jørgensen, K. A. J. Org. Chem. 2003, 68, 4151.
16. (b) Hechavarria Fonseca, M. T.; List, B. Angew. Chem., Int. Ed. 2004, 43, 3958.
17. (c) Peelen, T. J.; Chi, Y.-G.; Gellman, S. H. J. Am. Chem. Soc. 2005, 127, 11598.
18. (d) Chi, Y.-G.; Gellman, S. H. Org. Lett. 2005, 7, 4253.
19. (e) Wang, J.; Li, H.; Zu, L.-S.; Wang, W. Adv. Synth. Catal. 2006, 348, 425.
20. Mossé, S.; Alexakis, A. Org. Lett, 2005, 7, 4361.
21. (a) List, B.; Pojarlier, P.; Martin, H. J. Org. Lett. 2001, 3, 2423.
22. (b) Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737.
23. (c) Ishii, T.; Fujioka, S.; Sekiguchi, Y.; Kotsuki, H. J. Am. Chem. Soc. 2004, 126, 9558.
24. (d) Ishii, T.; Fujioka, S.; Sekiguchi, Y.; Kotsuki, H. J. Am. Chem. Soc. 2004, 126, 9558.
25. (e) Kotrusz, P.; Toma, S.; Schmalz, H. G.; Adler, A. Eur. J. Org. Chem. 2004, 1577.
26. (f) Mitchell, C. E. T.; Cobb, A. J. A.; Ley, S. V. Synlett 2005, 4, 611.
27. (g) Wang, W.; Wang, J.; Hao, H. Angew. Chem., Int. Ed. 2005, 44, 1369.
28. (h) Hayashi, Y.; Gotoh, H.; Hayashi, T.; Shoji, M. Angew. Chem., Int. Ed. 2005, 44, 4212.
29. (i) Xu, Y.-M.; Córdova, A. Chem. Commun. 2006, 460.
30. (j) Xu, Y.-M.; Zou, W.-B.; Sundén, H.; Ibrahem, I.; Cordova, A. Adv. Synth. Catal. 2006, 348, 418.
31. (k) Cao, C.-L.; Ye, M.-C.; Sun, X.-L.; Tang, Y. Org. Lett. 2006, 8, 2901.
32. (l) Luo, S.-Z.; Mi, X.-L.; Liu, S.; Xu, H.; Cheng, J.-P. Angew. Chem., Int. Ed. 2006, 45, 3039.
33. (m) Zu, L.-S.; Wang, J.; Li, H.; Wang, W. Org. Lett. 2006, 8, 3077.
34. (n) Wang, J.; Hao, H.; Lou, B.; Zu, L.-S.; Guo, H.; Wang, W. Chem. - Eur. J. 2006, 12, 4321.
35. (o) Huang, H.-B.; Jacobsen, E. N. J. Am. Chem. Soc. 2006, 128, 7170.
36. (p) Pansare, S. V.; Pandya, K. J. Am. Chem. Soc. 2006, 128, 9624.
37. (q) Tsogoeva, S. B.; Wei, S.-W. Chem. Commun. 2006, 1451.
38. (r) Cao, Y.-J.; Lai, Y.-Y.; Wang, X.; Li, Y.-J.; Xiao, W.-J. Tetrahedron Lett. 2007, 48, 21.
39. (a) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441.
40. (b) Betancort, J. M.; Sak, K.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Synthesis 2004, 9, 1509.
41. For alkylidene malonates as Michael acceptors in asymmetric catalysis, see: (a) Zhuang, W.; Hansen, T.; Jørgensen, K. A. Chem. Commun. 2001, 347.
42. (b) Yamazaki, S.; Iwata, Y. J. Org. Chem. 2006, 71, 739.
43. (c) Zhou, J.; Tang, Y. Chem. Commun. 2004, 432.
44. (d) Zhou, J.; Tang, Y. J. Am. Chem. Soc. 2002, 124, 9030.
45. (e) Zhou, J.; Ye, M.-C.; Huang, Z.-Z.; Tang, Y. J. Org. Chem. 2004, 69, 1309.
46. (f) Zhou, J.; Ye, M.-C.; Tang, Y. J. Comb. Chem. 2004, 6, 301.
47. (g) Ye, M.-C.; Li, B.; Zhou, J.; Sun, X.-L.; Tang, Y. J. Org. Chem. 2005, 70, 6108.
48. (h) Rasappan, R.; Hager, M.; Gissibl, A.; Reiser, O. Org. Lett. 2006, 8, 6099.
49. For chiral urea- and thiourea-catalyzed reactions, please see: (a) Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520.
50. (b) Herrera, R. P.; Sgarzani, V.; Bernardi, L.; Ricci, A. Angew. Chem., Int. Ed. 2005, 44, 6576.
51. (c) McCooey, S. H.; Connon, S. J. Angew. Chem., Int. Ed. 2005, 44, 6367.
52. (d) Wang, J.; Li, H.; Yu, X.-H.; Zu, L.-S.; Wang, W. Org. Lett. 2005, 7, 4293.
53. (e) Okinoi, T.; Hoashi, Y.; Furukawa, T.; Xu, X.-N.; Takemoto. Y. J. Am. Chem. Soc. 2005, 127, 119.
54. (f) Berkessel, A.; Cleemann, F.; Mukherjee, S.; Muller, T. N.; Lex, J. Angew. Chem., Int. Ed. 2005, 44, 807.
55. (g) Yoon, T. P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2005, 44, 466.
56. (h) Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 10558.
57. (i) Joly, G. D.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 4102.
58. (j) Sohtome, Y.; Tanatani, A.; Hashimoto, Y.; Nagasawa, K. Chem. Pharm. Bull. 2004, 52, 477.
59. (k) Sohtome, Y.; Tanatani, A.; Hashimoto, Y.; Nagasawa, K. Tetrahedron Lett. 2004, 45, 5589.
60. (l) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964.
61. (m) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012.
62. (n) Su, J. T.; Vachal, P.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 197.
63. (o) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279.
64. (p) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867.
65. (q) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.