Organocatalytic asymmetric aldol reaction of ketones with β,γ-unsaturated α-keto esters: An efficient access to chiral tertiary alcohol skeletons

Advanced Synthesis and Catalysis

Volumn 353, Issue 7, 2011, Pages 1179-1184

  Li, Pengfei ^a   Chan, Sau Hing ^a   Chan, Albert S C ^a   Kwong, Fuk Yee ^a  

^a HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

hydroxy carbonyl compounds; aldol reaction; esters; ketones; organocatalysis

Indexed keywords

EID: 79955926634     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000982     Document Type: Article

References (67)

1. For selected reviews, see K. Fuji, Chem. Rev. 1993, 93, 2037
2. E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402
3. Angew. Chem. Int. Ed. 1998, 37, 388
4. J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725
5. Angew. Chem. Int. Ed. 2001, 40, 4591
6. J. Christoffers, Chem. Eur. J. 2003, 9, 4862.
7. For selected examples of construction of quaternary stereocenters, see H. Li, J. Song, X. Liu, L. Deng, J. Am. Chem. Soc. 2005, 127, 8948
8. H. Li, Y. Wang, L. Tang, F. Wu, X. Liu, C. Guo, B. M. Foxman, L. Deng, Angew. Chem. 2005, 117, 107
9. Angew. Chem. Int. Ed. 2005, 44, 105
10. F. Wu, H. Li, R. Hong, L. Deng, Angew. Chem. 2006, 118, 961
11. Angew. Chem. Int. Ed. 2006, 45, 947
12. F. Wu, R. Hong, J. Khan, X. Liu, L. Deng, Angew. Chem. 2006, 118, 4407
13. Angew. Chem. Int. Ed. 2006, 45, 4301
14. Y. Wang, X. Liu, L. Deng, J. Am. Chem. Soc. 2006, 128, 3928
15. S. E. Denmark, T. W. Wilson, M. T. Burk, J. R. Heemstra Jr, J. Am. Chem. Soc. 2007, 129, 14864
16. H. Xie, L. Zu, H. Li, J. Wang, W. Wang, J. Am. Chem. Soc. 2007, 129, 10886
17. P. Li, Y. Wang, X. Liang, J. Ye, Chem. Commun. 2008, 3302
18. C. Baudequin, A. Zamfir, S. B. Tsogoeva, Chem. Commun. 2008, 4637
19. Y. Li, Z.-A. Zhao, H. He, S.-L. You, Adv. Synth. Catal. 2008, 350, 1885
20. B. Jiang, J. J. Dong, Y. G. Si, X. L. Zhao, Z. G. Huang, M. Xu, Adv. Synth. Catal. 2008, 350, 1360.
21. For some selected references, see C. H. Senanayake, K. Fang, P. Grover, R. P. Bakale, C. P. Vandenbossche, S. A. Wald, Tetrahedron Lett. 1999, 40, 819
22. P. T. Grover, N. N. Bhongle, S. A. Wald, C. H. Senanayake, J. Org. Chem. 2000, 65, 6283
23. S. Masumoto, M. Suzuki, M. Kanai, M. Shibasaki, Tetrahedron Lett. 2002, 43, 8647
24. P. Gupta, R. A. Fernandes, P. Kumar, Tetrahedron Lett. 2003, 44, 4231
25. S. Masumoto, M. Suzuki, M. Kanai, M. Shibasaki, Tetrahedron 2004, 60, 10497.
26. For selected reviews, see H. Gröger, E. M. Vogl, M. Shibasaki, Chem. Eur. J. 1998, 4, 1137
27. R. Mahrwald, Chem. Rev. 1999, 99, 1095
28. S. Denmark, R. A. Stavenger, Acc. Chem. Res. 2000, 33, 432
29. T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406
30. Angew. Chem. Int. Ed. 2000, 39, 1352
31. B. List, Tetrahedron 2002, 58, 5573
32. C. Palomo, M. Oiarbide, J. M. García, Chem. Soc. Rev. 2004, 33, 65
33. S. Saito, H. Yamamoto, Acc. Chem. Res. 2004, 37, 570
34. W. Notz, F. Tanaka, C. F. Barbas III, Acc. Chem. Res. 2004, 37, 580.
35. For reviews on primary amine catalytic aldol reaction, see A. Erkkilä, I. Majander, P. M. Pihko, Chem. Rev. 2007, 107, 5416
36. S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471
37. L.-W. Xu, Y. Lu, Org. Biomol. Chem. 2008, 6, 2047
38. F. Peng, Z. Shao, J. Mol. Catal. A: Chem. 2008, 285, 1
39. Y.-C. Chen, Synlett 2008, 1919
40. L.-W. Xu, J. Luo, Y. Lu, Chem. Commun. 2009, 1807.
41. For selected references on the aldolization of α-keto esters, see D. A. Evans, M. C. Kozlowski, C. S. Burgey, D. W. C. MacMillan, J. Am. Chem. Soc. 1997, 119, 7893
42. A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620
43. B. Jiang, Z. Chen, X. Tang, Org. Lett. 2002, 4, 3451
44. O. Tokuda, T. Kano, W.-G. Gao, T. Ikemoto, K. Maruoka, Org. Lett. 2005, 7, 5103
45. L. C. Akullian, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2006, 128, 6532
46. S. Samanta, C.-G. Zhao, J. Am. Chem. Soc. 2006, 128, 7442
47. K. Mikami, Y. Kawakami, K. Akiyama, K. Aikawa, J. Am. Chem. Soc. 2007, 129, 12950
48. F. Wang, Y. Xiong, X. Liu, X. Feng, Adv. Synth. Catal. 2007, 349, 2665
49. A. Yanagisawa, Y. Terajima, K. Sugita, K. Yoshida, Adv. Synth. Catal. 2009, 351, 1757
50. Z. Jiang, Y. Lu, Tetrahedron Lett. 2010, 51, 1884.
51. C. Zheng, Y. Wu, X. Wang, G. Zhao, Adv. Synth. Catal. 2008, 350, 2690.
52. C.-L. Cao, X.-L. Sun, Y.-B. Kang, Y. Tang, Org. Lett. 2007, 9, 4151.
53. P. Li, J. Zhao, F. Li, A. S. C. Chan, F. Y. Kwong, Org. Lett. 2010, 12, 5616.
54. For selected references, see J.-W. Xie, W. Chen, R. Li, M. Zeng, W. Du, L. Yue, Y.-C. Chen, Y. Wu, J. Zhu, J.-G. Deng, Angew. Chem. 2007, 119, 393
55. Angew. Chem. Int. Ed. 2007, 46, 389
56. J.-W. Xie, L. Yue, W. Chen, W. Du, J. Zhu, J.-G. Deng, Y.-C. Chen, Org. Lett. 2007, 9, 413
57. W. Chen, W. Du, L. Yue, R. Li, Y. Wu, L.-S. Ding, Y.-C. Chen, Org. Biomol. Chem. 2007, 5, 816
58. B.-L. Zheng, Q.-Z. Liu, C.-S. Guo, X.-L. Wang, L. He, Org. Biomol. Chem. 2007, 5, 2913
59. S. H. McCooey, S. J. Connon, Org. Lett. 2007, 9, 599
60. G. Bartoli, M. Bosco, A. Carlone, F. Pesciaioli, L. Sambri, P. Melchiorre, Org. Lett. 2007, 9, 1403
61. W. Chen, W. Du, Y.-Z. Duan, Y. Wu, S.-Y. Yang, Y.-C. Chen, Angew. Chem. 2007, 119, 7811
62. Angew. Chem. Int. Ed. 2007, 46, 7667
63. P. Ricci, A. Carlone, G. Bartoli, M. Bosco, L. Sambri, P. Melchiorre, Adv. Synth. Catal. 2008, 350, 49
64. J. Zhou, V. Wakchaure, P. Kraft, B. List., Angew. Chem. 2008, 120, 7768
65. Angew. Chem. Int. Ed. 2008, 47, 7656
66. P. Kwiatkowski, T. D. Beeson, J. C. Conrad, D. W. C. MacMillan, J. Am. Chem. Soc. 2011, 133, 1738.
67. 4, unit cell parameters: a=5.8161(3), b=9.8263(4), c=31.1263(15), space group P212121] contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.