Highly enantioselective alkenylation of cyclic α,β-unsaturated carbonyl compounds as catalyzed by a rhodium-diene complex: Application to the synthesis of (S)-pregabalin and (-)-α-kainic acid

Chemistry - A European Journal

Volumn 18, Issue 42, 2012, Pages 13274-13278

  Yu, Hong Jie ^a   Shao, Cheng ^a   Cui, Zhe ^a   Feng, Chen Guo ^a   Lin, Guo Qiang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

alkenylation; asymmetric catalysis; conjugate addition; diene ligands; rhodium

Indexed keywords

ASYMMETRIC CATALYSIS; CONCISE SYNTHESIS; CONJUGATE ADDITION; DIENE LIGANDS; ENANTIOSELECTIVE; HIGH YIELD; KAINIC ACID; UNSATURATED CARBONYL COMPOUNDS;

ADDITION REACTIONS; ALKENYLATION; AMINO ACIDS; CARBONYL COMPOUNDS; CATALYSIS; ENANTIOSELECTIVITY; OLEFINS; RHODIUM;

RHODIUM COMPOUNDS;

4 AMINOBUTYRIC ACID; ALKENE; COORDINATION COMPOUND; DRUG DERIVATIVE; KAINIC ACID; KETONE; PREGABALIN; RHODIUM;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKENES; CATALYSIS; COORDINATION COMPLEXES; GAMMA-AMINOBUTYRIC ACID; KAINIC ACID; KETONES; RHODIUM; STEREOISOMERISM;

EID: 84867229020     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201202660     Document Type: Article

References (80)

1. T. Hayashi, Synlett 2001, 879
2. T. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103, 2829
3. K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169
4. C. Gennari, C. Monti, U. Piarulli, Pure Appl. Chem. 2006, 78, 303
5. J. Christoffers, G. Koripelly, A. Rosiak, M. Rössle, Synthesis 2007, 1279
6. H. J. Edwards, J. D. Hargrave, S. D. Penrose, C. G. Frost, Chem. Soc. Rev. 2010, 39, 2093.
7. Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine, and Materials, 2 nd ed., (Ed: D. G. Hall,), Wiley-VCH, Weinheim, 2011.
8. Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, N. Miyaura, J. Am. Chem. Soc. 1998, 120, 5579.
9. Y. Takaya, M. Ogasawara, T. Hayashi, Tetrahedron Lett. 1998, 39, 8479
10. A. Duursma, J. G. Boiteau, L. Lefort, J. A. F. Boogers, A. H. M. de Vries, J. G. de Vries, A. J. Minnaard, B. L. Feringa, J. Org. Chem. 2004, 69, 8045
11. R. T. Stemmler, C. Bolm, J. Org. Chem. 2005, 70, 9925
12. G. Lalic, E. J. Corey, Tetrahedron Lett. 2008, 49, 4894
13. K. Okamoto, T. Hayashi, V. H. Rawal, Org. Lett. 2008, 10, 4387
14. R. Shintani, Y. Ichikawa, K. Takatsu, F.-X. Chen, T. Hayashi, J. Org. Chem. 2009, 74, 869
15. C. M. König, B. Gebhardt, C. Schleth, M. Dauber, U. Koert, Org. Lett. 2009, 11, 2728
16. T. Gendrineau, J.-P. Genet, S. Darses, Org. Lett. 2009, 11, 3486
17. B. Gebhardt, C. M. Koenig, C. Schleth, M. Dauber, U. Koert, Chem. Eur. J. 2010, 16, 5934
18. Y. Wang, X. Hu, H. Du, Org. Lett. 2010, 12, 5482
19. G. Pattison, G. Piraux, H. W. Lam, J. Am. Chem. Soc. 2010, 132, 14373
20. G. Chen, J. Gui, L. Li, J. Liao, Angew. Chem. 2011, 123, 7823
21. Angew. Chem. Int. Ed. 2011, 50, 7681
22. T. Thaler, L.-N. Guo, A. K. Steib, M. Raducan, K. Karaghiosoff, P. Mayer, P. Knochel, Org. Lett. 2011, 13, 3182
23. B. M. Trost, A. C. Burns, T. Tautz, Org. Lett. 2011, 13, 4566.
24. V. Hickmann, M. Alcarazo, A. Fürster, J. Am. Chem. Soc. 2010, 132, 11042
25. V. Hickmann, A. Kondoh, B. Gabor, M. Alcarazo, A. Fürstner, J. Am. Chem. Soc. 2011, 133, 13471.
26. S. Oi, Y. Honma, Y. Inoue, Org. Lett. 2002, 4, 667
27. S. Oi, A. Taira, Y. Honma, Y. Inoue, Org. Lett. 2003, 5, 97
28. Y. Otomaru, T. Hayashi, Tetrahedron: Asymmetry 2004, 15, 2647
29. Y. Nakao, J. Chen, H. Imanaka, T. Hiyama, Y. Ichikawa, W.-L. Duan, R. Shintani, T. Hayashi, J. Am. Chem. Soc. 2007, 129, 9137
30. S. Oi, T. Sato, Y. Inoue, Tetrahedron Lett. 2004, 45, 5051.
31. A. El-Batta, T. R. Hage, S. Plotkin, M. Bergdahl, Org. Lett. 2004, 6, 107
32. A. Alexakis, V. Albrow, K. Biswas, M. d'Augustin, O. Prieto, S. Woodward, Chem. Commun. 2005, 2843
33. K.-S. Lee, A. H. Hoveyda, J. Org. Chem. 2009, 74, 4455
34. D. Müller, C. Hawner, M. Tissot, L. Palais, A. Alexakis, Synlett 2010, 1694
35. D. Müller, M. Tissot, A. Alexakis, Org. Lett. 2011, 13, 3040
36. D. Müller, A. Alexakis, Org. Lett. 2012, 14, 1842.
37. G. A. Molander, R. Figueroa, Aldrichimica Acta 2005, 38, 49
38. H. A. Stefani, R. Cella, A. S. Vieira, Tetrahedron 2007, 63, 3623
39. G. A. Molander, N. Ellis, Acc. Chem. Res. 2007, 40, 275
40. S. Darses, J.-P. Genet, Chem. Rev. 2008, 108, 288.
41. M. Pucheault, S. Darses, J. P. Genet, Tetrahedron Lett. 2002, 43, 6155
42. M. Pucheault, S. Darses, J. P. Genet, Eur. J. Org. Chem. 2002, 3552.
43. J. B. Johnson, T. Rovis, Angew. Chem. 2008, 120, 852
44. Angew. Chem. Int. Ed. 2008, 47, 840
45. C. Defieber, H. Grutzmacher, E. M. Carreira, Angew. Chem. 2008, 120, 4558
46. Angew. Chem. Int. Ed. 2008, 47, 4482
47. R. Shintani, T. Hayashi, Aldrichimica Acta 2009, 42, 31
48. C.-G. Feng, M.-H. Xu, G.-Q. Lin, Synlett 2011, 1345.
49. C. Shao, H.-J. Yu, N.-Y. Wu, P. Tian, R. Wang, C.-G. Feng, G.-Q. Lin, Org. Lett. 2011, 13, 788.
50. Z. Cui, H.-J. Yu, R.-F. Yang, W.-Y. Gao, C.-G. Feng, G.-Q. Lin, J. Am. Chem. Soc. 2011, 133, 12394.
51. T. Hayashi, K. Ueyama, N. Tokunaga, K. Yoshida, J. Am. Chem. Soc. 2003, 125, 11508.
52. T. Mita, K. Sasaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2005, 127, 514
53. A. Armstrong, N. J. Convine, M. E. Popkin, Synlett 2006, 1589
54. V. Rodríguez, L. Quintero, F. Sartillo-Piscil, Tetrahedron Lett. 2007, 48, 4305
55. S. Poe, M. Kobaslija, T. McQuade, J. Am. Chem. Soc. 2007, 129, 9216
56. T. Ok, A. Jeon, J. Lee, J. H. Lim, C. S. Hong, H.-S. Lee, J. Org. Chem. 2007, 72, 7390
57. Z. Hamerak, I. Stipetić, A. Avdagić, Tetrahedron: Asymmetry 2007, 18, 1481
58. H. Gotoh, H. Ishikawa, Y. Hayashi, Org. Lett. 2007, 9, 5307
59. M. Ordóñez, C. Cativiela, Tetrahedron: Asymmetry 2007, 18, 3
60. C. A. Martinez, S. Hu, Y. Dumond, J. Tao, P. Kelleher, L. Tully, Org. Process Res. Dev. 2008, 12, 392
61. O. Bassas, J. Huuskonen, K. Rissanen, A. M. P. Koskinen, Eur. J. Org. Chem. 2009, 1340
62. J.-M. Liu, X. Wang, Z.-M. Ge, Q. Sun, T.-M. Cheng, R.-T. Li, Tetrahedron 2011, 67, 636.
63. S. Murakami, T. Takemoto, Z. Shimizu, J. Pharm. Soc. Jpn. 1953, 73, 1026.
64. E. G. MacGeer, J. W. Olney, P. L. MacGeer, Kainic Acid as a Tool in Neurobiology, Raven, New York, 1978.
65. J.-F. Tremblay, Chem. Eng. News 2000, 78, 14
66. J.-F. Tremblay, Chem. Eng. News 2000, 78, 31
67. J.-F. Tremblay, Chem. Eng. News 2001, 79, 19.
68. Y. C. Jung, C. H. Yoon, E. Turos, K. S. Yoo, K. W. Jung, J. Org. Chem. 2007, 72, 10114
69. K. Tomooka, T. Akiyama, P. Man, M. Suzuki, Tetrahedron Lett. 2008, 49, 6327
70. M. S. Majik, P. S. Parameswaran, S. G. Tilve, J. Org. Chem. 2009, 74, 3591
71. A. Farwick, G. Helmchen, Org. Lett. 2010, 12, 1108
72. K. Kitamoto, M. Sampei, Y. Nakayama, T. Sato, N. Chida, Org. Lett. 2010, 12, 5756
73. G. Lemie're, S. Sedehizadeh, J. Toueg, N. Fleary-Roberts, J. Clayden, Chem. Commun. 2011, 47, 3745
74. S. Takita, S. Yoloshima, T. Fukuyama, Org. Lett. 2011, 13, 2068
75. T. Kamon, Y. Irifune, T. Tanaka, T. Yoshimitsu, Org. Lett. 2011, 13, 2674
76. M. A. Lowe, M. Ostovar, S. Ferrini, C. C. Chen, P. G. Lawrence, F. Fontana, A. A. Calabrese, V. K. Aggarwal, Angew. Chem. 2011, 123, 6494
77. Angew. Chem. Int. Ed. 2011, 50, 6370
78. G. Wei, J. M. Chalker, T. Cohen, J. Org. Chem. 2011, 76, 7912
79. P. J. Parsons, S. P. G. Rushton, R. R. Panta, A. J. Murray, M. P. Coles, J. Lai, Tetrahedron 2011, 67, 10267.
80. During the preparation of this manuscript, a rhodium-catalyzed conjugate-addition reaction of alkenylboronic acids to cyclic enones with similar bicyclo[3.3.0]octa-2,5-diene ligands was reported:, S. Helbig, K. V. Axenov, S. Tussetschläger, W. Frey, S. Laschat, Tetrahedron Lett. 2012, 53, 3506.