An unexpected inversion of enantioselectivity in the proline catalyzed intramolecular Baylis-Hillman reaction

Tetrahedron Letters

Volumn 46, Issue 51, 2005, Pages 8899-8903

  Chen, Shang Hung ^a   Hong, Bor Cherng ^a   Su, Cheng Feng ^a   Sarshar, Sepehr ^b  

^a NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

^b Auspex Pharmaceuticals   (United States)

Author keywords

Baylis Hillman; Intramolecular; Inversion; Proline

Indexed keywords

IMIDAZOLE; PROLINE;

ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; ENANTIOSELECTIVITY; MOLECULAR BIOLOGY;

EID: 27944479071     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.072     Document Type: Article

References (83)

1. For reviews, see: A.M. Rouhi Chem. Eng. News 2004 41
2. P.I. Dalko, and L. Moisan Angew. Chem., Int. Ed. 43 2004 5138
3. J. Seayad, and B. List Org. Biomol. Chem. 3 2005 719
4. A. Berkessel, and H. Gröger Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis 2005 Wiley New York
5. (a) For the recent reviews, see: B. List Tetrahedron 58 2002 5573
6. W. Notz, F. Tanaka, and C.F. Barbas Acc. Chem. Res. 37 2004 580
7. D.M. Mans, and W.H. Pearson Org. Lett. 6 2004 3305
8. R. Thayumanavan, F. Tanaka, and C.F. Barbas Org. Lett. 6 2004 3541
9. (d) For a two-step proline catalyzed synthesis of carbohydrates, see: A.B. Northrup, I.K. Mangion, F.H. Hettche, and D.W.C. MacMillan Angew. Chem., Int. Ed. 43 2004 2152
10. A.B. Northrup, and D.W.C. MacMillan Science 305 2004 1752
11. K.A. Ahrendt, C.J. Borths, and D.W.C. MacMillan J. Am. Chem. Soc. 122 2000 4243
12. N.S. Chowdari, J.T. Suri, and C.F. Barbas Org. Lett. 6 2004 2507
13. B. List J. Am. Chem. Soc. 122 2000 9336
14. N. Mase, R. Thayumanavan, F. Tanaka, and C.F. Barbas Org. Lett. 6 2004 2527
15. M.T.H. Fronseca, and B. List Angew. Chem., Int. Ed. 43 2004 3958
16. O. Andrey, A. Alexakis, and G. Bernardinelli Org. Lett. 5 2003 2559
17. C. Pidathala, L. Hoang, N. Vignola, and B. List Angew. Chem., Int. Ed. 42 2003 2785
18. S. Chandrasekhar, C. Narsihmulu, N.R. Reddy, and S.S. Sultana Chem. Commun. 2004 2450
19. Q. Pan, B. Zou, Y. Wang, and D. Ma Org. Lett. 6 2004 1009
20. K. Juhl, and K.A. JøÍrgensen Angew. Chem., Int. Ed. 42 2003 1498
21. D.B. Ramchary, N.S. Chowdari, and C.F. Barbas Angew. Chem., Int. Ed. 42 2003 4233
22. A.B. Northrup, and D.W.C. MacMillan J. Am. Chem. Soc. 124 2002 2458
23. B. List J. Am. Chem. Soc. 124 2002 5656
24. N. Kumaragurubaran, K. Juhl, W. Zhuang, A. Bogevig, and K.A. Jorgensen J. Am. Chem. Soc. 124 2002 6254
25. A. Bogevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, and K.A. Jorgensen Angew. Chem., Int. Ed. 41 2002 1790
26. N. Vignola, and B. List J. Am. Chem. Soc. 125 2003 450
27. W. Wang, J. Wang, and H. Li Org. Lett. 6 2004 2817
28. For reviews, see: D. Basavaiah, A.J. Rao, and T. Satyanarayana Chem. Rev. 103 2003 811
29. P. Langer Angew. Chem., Int. Ed. 39 2000 3049
30. D. Basavaiah, P.D. Rao, and R.S. Hyma Tetrahedron 24 1996 8001
31. D.J. Mergott, S.A. Frank, and W.R. Roush Proc. Natl. Acad. Sci. U.S.A. 101 2004 11955
32. P.R. Krishna, M. Narsingam, and V. Kannan Tetrahedron Lett. 45 2004 4773
33. B.M. Trost, O.R. Thiel, and H.-C. Tsui J. Am. Chem. Soc. 125 2003 13155
34. W.P. Almeida, and F. Coelho Tetrahedron Lett. 44 2003 937
35. B.M. Trost, O.R. Thiel, and H.-C. Tsui J. Am. Chem. Soc. 124 2002 11616
36. C.R. Mateus, M.P. Feltrin, A.M. Costa, F. Coelho, and W.P. Almeida Tetrahedron 57 2001 6901
37. B. Wang, X.-M. Yu, and G.-Q. Lin Synlett Spec. issue 2001 904
38. J. Jauch Eur. J. Org. Chem. 3 2001 473
39. Y. Iwabuchi, M. Furukawa, T. Esumi, and S. Hatakeyama Chem. Commun. 2001 2030
40. J. Jauch Angew. Chem., Int. Ed. 39 2000 2764
41. K.E. Price, S.J. Broadwater, H.M. Jung, and D.T. McQuade Org. Lett. 7 2005 147
42. M.L. Bode, and P.T. Kaye Tetrahedron Lett. 32 1991 5611
43. P.R. Krishna, V. Kannan, and G.V.M. Sharma J. Org. Chem. 69 2004 6467
44. J.E. Yeo, X. Yang, H.J. Kim, and S. Koo Chem. Commun. 2004 236
45. G.E. Keck, and D.S. Welch Org. Lett. 4 2002 3687
46. S.A. Frank, D.J. Mergott, and W.R. Roush J. Am. Chem. Soc. 124 2002 2404
47. G.F. Black, F. Dinos, S. Fratuccello, F.J. Murphy, M. Nielsen, and H.L. Williams Tetrahedron Lett. 38 1997 8561
48. F. Roth, P. Gygax, and G. Fráter Tetrahedron Lett. 33 1992 1045
49. M. Shi, J.-K. Jiang, and C.-Q. Li Tetrahedron Lett. 43 2002 127
50. J.E. Imbriglio, M.M. Vasbinder, and S.J. Miller Org. Lett. 5 2003 3741
51. For recent examples in asymmetric intermolecular B-H reaction, see: A.G.M. Barrett, A.S. Cook, and A. Kamimura Chem. Commun. 1998 2533
52. M. Shi, and J.-K. Jiang Tetrahedron: Asymmetry 13 2002 1941
53. D. Balan, and H. Adolfsson Tetrahedron Lett. 44 2003 2521
54. N.T. McDougal, and S.E. Schaus J. Am. Chem. Soc. 125 2003 12094
55. Y. Hayashi, T. Tamura, and M. Shoji Adv. Synth. Catal. 346 2004 1106
56. B. Pegot, G. Vo-Thanh, D. Gori, and A. Loupy Tetrahedron Lett. 45 2004 6425
57. P.R. Krishna, V. Kannan, and P.V.N. Reddy Adv. Synth. Catal. 346 2004 603
58. Y. Sohtome, A. Tanatani, Y. Hashimoto, and K. Nagasawa Tetrahedron Lett. 45 2004 5589
59. C.M. Mocquet, and S.L. Warriner Synlett 2 2004 356
60. S. Kawahara, A. Nakano, T. Esumi, Y. Iwabuchi, and S. Hatakeyama Org. Lett. 5 2003 3103
61. K.-S. Yang, W.-D. Lee, J.-F. Pan, and K. Chen J. Org. Chem. 68 2003 915
62. M. Shi, and Y.-M. Xu Angew. Chem., Int. Ed. 41 2002 4507
63. V.K. Aggarwal, A.M. Castro, A. Mereu, and H. Adams Tetrahedron Lett. 43 2002 1577
64. Y. Iwabuchi, M. Furukawa, T. Esumi, and S. Hatakeyama Chem. Commun. 19 2001 2030
65. Y. Iwabuchi, M. Nakatani, N. Yokoyama, and S. Hatakeyama J. Am. Chem. Soc. 121 1999 10219
66. T. Hayase, T. Shibata, K. Soai, and Y. Wakatsuki Chem. Commun. 12 1998 1271
67. I.E. Mark, P.R. Giles, and N.J. Hindley Tetrahedron Lett. 53 1997 1015
68. M. Shi, Y.-M. Xu, G.-L. Zhao, and X.-F. Wu Eur. J. Org. Chem. 2002 3666 3679
69. M. Shi, and Y.-M. Xu Eur. J. Org. Chem. 2002 696 701
70. 3), see: S. Takano, T. Yamane, M. Takahashi, and K. Ogasawara Tetrahedron: Asymmetry 3 1992 837
71. 4 followed by hydrogenation (cat. Pt/C, MeOH), see: D. Buisson, and R. Azerad Tetrahedron Lett. 27 1986 2631 2634
72. J. Weidner, F. Theil, and H. Schick Tetrahedron: Asymmetry 5 1994 751 754
73. K. Inoguchi, N. Fujie, K. Yoshikawa, and K. Achiwa Chem. Pharm. Bull. 40 1992 2921 2926
74. To the best of our knowledge, such an inversion of enantioselectivity is unprecedented. For an example of solvent mediated inversion of enzymatic enantioselectivity, see: S. Tawaki, and A. Klibanov J. Am. Chem. Soc. 114 1992 1882
75. (b) For an example of solvent mediated inversion of enantioselectivity in platinum-catalyzed hydrogenation, see: R. Hess, A. Vargas, T. Mallat, T. Bürgi, and A. Baiker J. Catal. 222 2004 117
76. M. Arx, T. Mallat, and A. Baiker Angew. Chem., Int. Ed. 40 2001 2302
77. TS A was reported to be more stable than B. For calculations and discussions on the transition states of proline-catalyzed aldol reactions, see: S. Bahmanyar, and K.N. Houk J. Am. Chem. Soc. 123 2001 11273
78. S. Bahmanyar, and K.N. Houk J. Am. Chem. Soc. 123 2001 12911
79. K.N. Rankin, J.W. Gauld, and R.J. Boyd J. Phys. Chem. A 106 2002 5155
80. S. Bahmanyar, K.N. Houk, H.J. Martin, and B. List J. Am. Chem. Soc. 125 2003 2475
81. L. Hoanh, S. Bahmanyar, K.N. Houk, and B. List J. Am. Chem. Soc. 125 2003 16
82. B. List Synlett 2001 1675
83. For the same reaction with proline derivatives, see: M.T.H. Fonseca, and B. List Angew. Chem., Int. Ed. 43 2004 3958