Organocatalyst-mediated enantioselective intramolecular Michael addition of aldehydes to vinyl sulfones

Tetrahedron Asymmetry

Volumn 21, Issue 13-14, 2010, Pages 1666-1673

  Bournaud, Chloée ^a   Marchal, Estelle ^a   Quintard, Adrien ^a   Sulzer Mossé, Sarah ^a   Alexakis, Alexandre ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2 (3,5 BIS TRIFLUOROMETHYL PHENYLSULFONYLMETHYL) CYCLOPENTANE CARBALDEHYDE; 2 (4 NITRO PHENYLSULFONYLMETHYL) CYCLOPENTANE CARBALDEHYDE; 2 (PYRIDINE 2 SULFONYLMETHYL)CYCLOPENTANE CARBALDEHYDE; 2 [4 (3,5 BIS(TRIFLUOROMETHYL)PHENYLSULFONYL)BUT 3 ENYL] [1,3] DITHIANE; 2 [6 (3,5 BIS TRIFLUOROMETHYL PHENYLSULFONYL)HEX 5 ENYL] [1,3]DITHIANE; 2 [6 (4 NITROPHENYLSULFONYL)HEX 5 ENYL] 1,3 DITHIANE; 2 [6 (PHENYLSULFONYL)HEX 5 ENYL] [1,3]DITHIANE; 2 PHENYLSULFONYLMETHYL CYCLOPENTANE CARBALDEHYDE; 4 (PHENYLSULFONYL)BUT 3 ENAL; 5 (PHENYLSULFONYL)PENT 4 ENAL; 5 [3,5 BIS (TRIFLUOROMETHYL) PHENYLSULFONYL)PENT 4 ENAL; 7 (3,5 BIS TRIFLUOROMETHYLPHENYLSULFONYL)HEPT 6 ENAL; 7 (4 NITRO PHENYLSULFONYL)HEPT 6 ENAL; 7 (PHENYLSULFONYL)HEPT 6 ENAL; 7 (PYRIDINE 2 SULFONYL)HEPT 6 ENAL; ALDEHYDE; SULFONE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; HYDROGEN BOND; MICHAEL ADDITION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TEMPERATURE MEASUREMENT;

EID: 77956266209     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.03.043     Document Type: Article

References (60)

1. For recent reviews on organocatalysis see: E.R. Jarvo, and S.J. Miller Tetrahedron 58 2002 2481
2. P.I. Dalko, and L. Moisan Angew. Chem., Int. Ed. 43 2004 5138
3. B. List, and J. Seayad Org. Biomol. Chem. 3 2005 719
4. M.J. Gaunt, C.C.C. Johson, A. McNally, and N.T. Vo Drug Discovery Today 12 2007 8
5. A. Dondoni, and A. Massi Angew. Chem., Int. Ed. 47 2008 4638
6. See also special issues on asymmetric organocatalysis: (f) Acc. Chem. Res. 2004, 37, issue 8
7. Adv. Synth. Catal. 2004, 346, issue 9-10
8. Chimia 2007, issue 5
9. Chem. Rev. 2007, issue 12
10. S. Bertelsen, and K.A. Jørgensen Chem. Soc. Rev. 38 2009 2178
11. B. List, R.A. Lerner, and C.F. Barbas III J. Am. Chem. Soc. 122 2000 2395
12. K.A. Ahrendt, C.J. Borths, and D.W.C. MacMillan J. Am. Chem. Soc. 122 2000 4243
13. For selected reviews on organocatalytic Michael addition see: S.B. Tsogoeva Eur. J. Org. Chem. 2007 1701
14. D. Almasi, D.A. Alonso, and C. Nájera Tetrahedron: Asymmetry 18 2007 299
15. S. Sulzer-Mossé, and A. Alexakis Chem. Commun. 2007 3123
16. N. Mase, K. Watanabe, H. Yoda, K. Takabe, F. Tanaka, and C.F. Barbas III J. Am. Chem. Soc. 128 2006 4966
17. J.M. Betancort, K. Sakthivel, R. Thayumanavan, and C.F. Barbas III Tetrahedron Lett. 42 2001 4441
18. J.M. Betancort, K. Sakthivel, R. Thayumanavan, F. Tanaka, and C.F. Barbas III Synthesis 2004 1509
19. C.-L. Cao, X.-L. Sun, J.-L. Zhou, and Y. Tang J. Org. Chem. 72 2007 4073
20. J. Wang, F. Yu, X. Zhang, and D. Ma Org. Lett. 10 2008 2561
21. Y. Hayashi, H. Gotoh, T. Hayashi, and M. Shoji Angew. Chem., Int. Ed. 44 2005 4212
22. J. Wang, H. Li, L. Zhu, and W. Wang Adv. Synth. Catal. 348 2006 425
23. P. Melchiorre, and K.A. Jørgensen J. Org. Chem. 68 2003 4151
24. Y. Chi, and S.H. Gellman Org. Lett. 7 2005 4253
25. T.J. Peelen, Y. Chi, and S.H. Gellman J. Am. Chem. Soc. 127 2005 11598
26. D.A. Alonso, S. Kitagaki, N. Utsumi, and C.F. Barbas III Angew. Chem., Int. Ed. 120 2008 4588
27. B. List, P. Pojarliev, and H.J. Martina Org. Lett. 16 2001 2423
28. S. Mukherjee, J.W. Yang, S. Hoffmann, and B. List Chem. Rev. 107 2007 5471
29. D. Enders, H. Wahl, and K. Papadopoulos Tetrahedron 53 1997 1291
30. M. Ruiz, O. Vicente, G. Shapiro, G. Shapiro, and H.-P. Weber Tetrahedron Lett. 35 1994 4551
31. A. Schick, T. Kolter, A. Giannis, and K. Sandhoff Tetrahedron 51 1995 11207
32. M.C. Fernandez, J.M. Quintela, M. Ruiz, and O. Vicente Tetrahedron: Asymmetry 13 2002 233
33. M.C. Fernandez, A. Diaz, J.J. Guillin, O. Blanco, and M. Vicente J. Org. Chem. 71 2006 6958
34. S. Sulzer-Mossé, M. Tissot, and A. Alexakis Org. Lett. 9 2007 3749
35. M. Capuzzi, D. Perdicchia, and K.A. Jørgensen Chem. Eur. J. 14 2008 128
36. S. Mossé, and A. Alexakis Org. Lett. 7 2005 4361
37. S. Sulzer-Mossé, A. Alexakis, J. Mareda, G. Bollot, G. Bernardinelli, and Y. Filinchuk Chem. Eur. J. 15 2009 3204
38. A. Quintard, C. Bournaud, and A. Alexakis Chem. Eur. J. 14 2008 7504
39. H. Li, S. Song, X. Liu, and L. Deng J. Am. Chem. Soc. 127 2005 8948
40. T.-Y. Liu, J. Long, B.-J. Li, L. Jiang, R. Li, Y. Wu, L.-S. Ding, and Y.-C. Chen Org. Biomol. Chem. 4 2006 2097
41. Q. Zhu, and Y. Lu Org. Lett. 11 2009 1721
42. S. Zhang, Y. Zhang, Y. Ji, and W. Wang Chem. Commun. 2009 4886
43. A. Quintard, and A. Alexakis Chem. Eur. J. 15 2009 11109 11113
44. A. Quintard, S. Belot, E. Marchal, and A. Alexakis Eur. J. Org. Chem. 2010 927
45. Y. Hayashi, H. Gotoh, T. Tamura, H. Yamaguchi, R. Masui, and M. Shoji J. Am. Chem. Soc. 127 2005 1608
46. M.T.H. Fonseca, and B. List Angew. Chem., Int. Ed. 43 2004 3958
47. M. Kikuchi, T. Inagaki, and H. Nishiyame Synlett 2007 1075
48. W.J. Nodes, D.R. Nutt, A.M. Chippindale, and A.J.A. Cobb J. Am. Chem. Soc. 131 2009 16016
49. E. Marqués-López, R.P. Herrera, T. Marks, W.C. Jacobs, D. Könning, RE M. de Figueiredo, and M. Christmann Org. Lett. 11 2009 4116
50. N.S. Simpkins Tetrahedron 46 1990 6951
51. D.C. Meadows, and J. Gerva-Hague Med. Res. Rev. 6 2006 793
52. Q. Zhu, L. Cheng, and Y. Lu Chem. Commun. 2008 6315
53. Q. Zhu, and Y. Lu Org. Lett. 10 2008 4803
54. A. Landa, M. Maestro, C. Masdeu, A. Puente, S. Vera, M. Oiarbide, and C. Palomo Chem. Eur. J. 15 2009 1562
55. H. Li, J. Song, and L. Deng Tetrahedron 65 2009 3139
56. C. Palomo, S. Vera, A. Mieglo, and E. Gomez-Bengoa Angew. Chem., Int. Ed. 45 2006 5984
57. M. Gibson, J.M. Goodman, L.J. Farrugia, and R.C. Hartley Tetrahedron Lett. 44 2003 2841
58. D. Enders, S. von Berg, and B. Jandeleit Org. Synth. 78 2002 169
59. P. Mauléon, and J.-C. Carretero Org. Lett. 6 2004 3195
60. D.A. Alonso, A. Babrowski, M. Fuensanta, C. Najera, and M. Varea Arkivoc 2007 243