A general organocatalyst for direct α-functionalization of aldehydes: Stereoselective C-C, C-N, C-F, C-Br, and C-S bond-forming reactions. Scope and mechanistic insights

Journal of the American Chemical Society

Volumn 127, Issue 51, 2005, Pages 18296-18304

  Franzén, Johan ^a   Marigo, Mauro ^a   Fielenbach, Doris ^a   Wabnitz, Tobias C ^a   Kjærsgaard, Anne ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYST SELECTIVITY; ETHERS; REACTION KINETICS;

ENANTIOSELECTIVITY; KINETIC RESOLUTION; NONLINEAR EFFECTS; ORGANOCATALYSTS; STEREOGENIC FORMATION;

CATALYSTS;

ALDEHYDE; PROLINOL SILYL ETHER DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL BOND; ENANTIOSELECTIVITY; NONLINEAR SYSTEM; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 29844457732     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja056120u     Document Type: Article

References (91)

1. For recent reviews on organocatalysis, see: (a) Dalko, P. L.; Moisan, L. Angew. Chem.. Int. Ed. 2004, 43, 5138.
2. (b) Berkessel, A.; Gröger, H. Asymmetric Organocatalysis; WCH: Weinheim, Germany, 2004.
3. (c) Seayed, J.; List, B. Org. Biomol. Chem. 2005, 3, 719.
4. (d) Jarvo, E. R.; Scott, J. M. Tetrahedron 2002, 58, 2481.
5. (e) List, B. Tetrahedron 2002, 58, 5573.
6. (f) List, B. Synlett 2001, 11, 1675.
7. (g) See also: Acc. Chem. Res. 2004, 37, number 8.
8. Special edition devoted to asymmetric organocatalysis. (2) For recent accounts, see: (a) Notz, W.; Tanaka, F.; Barbas, C. F., III. Acc. Chem. Res. 2004, 37, 580.
9. (b) List, B. Acc. Chem. Res. 2004, 37, 548.
10. (c) Córdova, A. Acc. Chem. Res. 2004, 37, 102.
11. (a) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790.
12. (b) List, B. J. Am. Chem. Soc. 2002, 124, 5656.
13. (c) Vogt, H.; Vanderheiden, S.; Brase, S. Chem. Commun. 2003, 2448.
14. (d) Suri, J. T.; Steiner, D. D.; Barbas, C. F., III. Org. Lett. 2005, 7, 3885.
15. (e) Chowdari, N. S.; Barbas, C. F., III. Org. Lett. 2005, 7, 867.
16. (f) Iwamura, H.; Mathew, S. P.; Blackmond, D. G. J. Am. Chem. Soc. 2004, 126, 11770.
17. For fluorination, see: (a) Steiner, D. D.; Mase, N.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2005, 44, 3706.
18. (b) Beeson, T. D.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 8826.
19. (c) Enders, D.; Hüttl, M. R. M. Synlett 2005, 991.
20. (d) Marigo, M.; Fielenbach, D.; Braunton, A.; Kjærsgaard, A.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2005, 44, 3703.
21. For chlorination, see: (e) Brochu, M. P.; Brown, S. P.; MacMillan, D. W. C. J. Am. Chem. Soc. 2004, 126, 4108.
22. (f) Hailand, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790.
23. For bromination, see: (g) Bertelsen, S.; Hailand, N.; Bachmann, S.; Marigo, M.; Braunton, A.; Jørgensen, K. A. Chem. Commun. 2005, 4821.
24. Marigo, M.; Wabnitz, T. C.; Fielenbach, D.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2005, 44, 794.
25. (a) Brown, S. P.; Brochu, M. P.; Sinz, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 10808.
26. (b) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247.
27. (c) Hayashi, Y.; Yamaguchi, J.; Hibino, K.; Shoji, M. Tetrahedron Lett. 2003, 44, 8293.
28. (d) Zhong, G.; Yu, Y. Org. Lett. 2004, 6, 1637.
29. (e) Córdova, A.; Sundén, H.; Bøgevig, A.; Johansson, M.; Himo F. Chem.-Eur. J. 2004, 10, 3673.
30. (f) Córdova, A.; Sundén, H.; Engqvist, M.; Ibrahem, I.; Casas, J. J. Am. Chem. Soc. 2004, 126, 8914.
31. (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395.
32. (b) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260.
33. (c) Córdova, A.; Notz, W.; Barbas, C. F., III. J. Org. Chem. 2002, 67, 301.
34. (d) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798.
35. (e) Bøgevig, A.; Kumaragurubaran, N.; Jørgensen, K. A. Chem. Commun. 2002, 620.
36. (f) Tang, Z.; Jiang, F.; Yu, L.-T.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262.
37. (g) Mase, N.; Tanaka, F.; Barbas, C. F., III. Angew. Chem., Int. Ed. 2004, 43, 2420.
38. (h) Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983.
39. (i) Artikka, A.; Arvidsson, P. I. Tetrahedron: Asymmetry 2004, 15, 1831.
40. (j) Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 3541.
41. (k) Kofoed, J.; Nielsen, J.; Reymond, J.-L. Bioorg. Med. Chem. Lett. 2003, 13, 2445.
42. (l) Chandrasekhar, S.; Narsihmulu, Ch.; Reddy, N. R.; Sultana, S. S. Chem. Commun. 2004, 2450.
43. (m) Allemann, C.; Gordillo, R.; Clemente, F. R.; Cheong, P. H.; Houk, K. N. Acc. Chem. Res. 2004, 37, 558.
44. (a) Notz, W.; Sakthivel, K.; Bui, T.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 199.
45. (b) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842.
46. (c) Córdova, A.; Watanabe, S.-I.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866.
47. (d) Chowdari, N. S.; Ramachary, D. B.; Barbas, C. F., III. Synlett. 2003, 1906.
48. (e) Notz, W.; Tanaka, F.; Watanabe, S.-I.; Chowdari, N. S.; Thayumanavan, R.; Barbas, C. F., III. J. Org. Chem. 2003, 68, 9624.
49. (f) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
50. (g) Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 558.
51. (h) Zhuang, W.; Saaby, S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 476.
52. (i) Chowdari, N. S.; Suri, J. T.; Barbas, C. F., III. Org. Lett. 2004, 6, 2507.
53. Mangion, I. K.; Northrup, A. B.; MacMillan, D. C. W. Angew. Chem., Int. Ed. 2004, 43, 6722.
54. (a) Allemann, C.; Gordillo, R.; Clemente, F. R.; Cheong, P. H.; Houk, K. N. Acc. Chem. Res. 2004, 37, 558.
55. (b) Cheong, P. H.-Y.; Houk, K. N. J. Am. Chem. Soc. 2004, 126, 13912.
56. (c) Bahmanyar, S.; Houk, K. N. Org. Lett 2003, 5, 1249.
57. (d) Bahmanyar, S.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 11273.
58. Juhl, K.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 1498.
59. For some comparing studies on the reactivity between compound 1 and 2a preformed within our group, see refs 4d, 4f, 5, 11, and 15d.
60. (a) Zuo, G.; Zhang, Q.; Xu, J. Heteroat. Chem. 2003, 14, 42.
61. (b) Okuyama, Y.; Nakano, H.; Hongo, H. Tetrahedron: Asymmetry 2000, 11, 1193.
62. Córdova, A.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 7749.
63. (a) Chi, Y.; Gellman, S. H. Org. Lett. 2005, 7, 4253.
64. (b) Hayashi, Y.; Gotoh, H.; Hayashi, T.; Shoji, M. Angew. Chem., Int. Ed. 2005, 44, 4212.
65. (c) Wang, W.; Wang, J.; Li, H. Angew. Chem., Int. Ed. 2005, 44, 1369.
66. (d) Melchiorre, P.; Jørgensen, K. A. J. Org. Chem. 2003, 68, 4151.
67. (e) Betancort, J. M.; Barbas, C. F., III. Org. Lett. 2001, 3, 3737.
68. (f) Mase, N.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2004, 6, 2527.
69. (g) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Tanaka, F.; Barbas. C. F., III. Synthesis 2004, 1509.
70. (h) Hechavarria Fonseca, M. T.; List, B. Angew. Chem., Int. Ed. 2004, 43, 3958.
71. (i) Peelen, T. J.; Chi, Y.; Gellman, S. H. J. Am. Chem. Soc. 2005, 127, 11598.
72. For examples: (a) Youn, J.-H.; Herrmann, R.; Ugi, I. Synthesis 1987, 158.
73. (b) Poli, G.; Belvisi, L.; Manzoni, L.; Scolastico, C. J. Org. Chem. 1993, 58, 3165.
74. (c) Enders, D.; Schäfer, T.; Piva, O.; Zamponi, A. Tetrahedron 1994, 50, 3349.
75. (d) Chibale, K.; Warren, S. Tetrahedron Lett. 1994, 35, 3991.
76. (e) Enders, D.; Schäfer, T.; Mies, W. Tetrahedron 1998, 54, 10239.
77. (f) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagné, M. R. J. Am. Chem. Soc. 2000, 122, 7905.
78. See also: (g) Jereb, M.; Togni, A. Org. Lett. 2005, 7, 4041.
79. (a) Wenig, W.; Li, H.; Wang, J.; Liao, L. Tetrahedron Lett. 2004, 45, 8229.
80. (b) Wang, W.; Wang, J.; Li, H. Org. Lett. 2004, 6, 2817.
81. (c) Wang, J.; Li, H.; Mei, Y.; Lou, B.; Xu, D.; Xie, D.; Guo, H.; Wang, W. J. Org. Chem. 2005, 70, 5678.
82. (a) Frisch, M. J. et al. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
83. (b) Frisch, M. J. et al. Gaussian 03, revision B.05; Gaussian, Inc.: Pittsburgh, PA, 2003.
84. The absolute configuration was determined by comparison of optical rotation with literature data. See Supporting Information for references.
85. (a) Taft, R. W., Jr. J. Am. Chem. Soc. 1952, 74, 2729.
86. (b) Taft, R. W., Jr. J. Am. Chem. Soc. 1952, 74, 3120.
87. (c) Taft, R. W., Jr. J. Am. Chem. Soc. 1953, 75, 4231.
88. (a) de Riggi, I.; Virgili, A.; de Moragas, M.; Jaime, C. J. Org. Chem. 1995, 60, 27.
89. (b) Wolf, C.; König, W. A.; Roussel, C. Liebigs Ann. 1995, 781.
90. (a) Marigo, M.; Franzén, J.; Poulsen, T. B.; Zhuang, W.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 6964.
91. (b) Marigo, M.; Schulte, T.; Franzén, J.; Jørgensen K. A. J. Am. Chem. Soc. 2005, 127, 15710.