Asymmetric inverse-electron-demand hetero-Diels-Alder reaction of six-membered cyclic ketones: An enamine/metal lewis acid bifunctional approach

Angewandte Chemie - International Edition

Volumn 50, Issue 15, 2011, Pages 3484-3488

  Xu, Zhenghu ^a   Liu, Lu ^a   Wheeler, Kraig ^b   Wang, Hong ^a  

^a MIAMI UNIVERSITY   (United States)

^b EASTERN ILLINOIS UNIVERSITY   (United States)

Author keywords

bifunctional catalysis; cyclic ketones; cycloadditions; Lewis acids; organocatalysis

Indexed keywords

BIFUNCTIONAL CATALYSIS; CYCLIC KETONES; CYCLOADDITIONS; LEWIS ACID; ORGANOCATALYSIS;

CYCLOADDITION; ENANTIOSELECTIVITY; ESTERS; KETONES; RATE CONSTANTS; REACTION KINETICS;

CATALYSIS;

EID: 79953243922     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201100160     Document Type: Article

References (51)

1. For reviews, see: a) Z. H. Shao, H. B. Zhang, Chem. Soc. Rev. 2009, 38, 2745
2. C. Zhong, X. D. Shi, Eur. J. Org. Chem. 2010, 2999; for examples, see
3. A. E. Allen, D. W. C. MacMillan, J. Am. Chem. Soc. 2010, 132, 4986
4. T. Yang, A. Ferrali, L. Campbell, D. J. Dixon, Chem. Commun. 2008, 2923
5. Q. P. Ding, J. Wu, Org. Lett. 2007, 9, 4959
6. I. Ibrahem, A. Cordova, Angew. Chem. 2006, 118, 1986
7. Angew. Chem. Int. Ed. 2006, 45, 1952
8. F. Bihelovic, R. Matovic, B. Vulovic, R. N. Saicic, Org. Lett. 2007, 9, 5063
9. I. Usui, S. Schmidt, B. Breit, Org. Lett. 2009, 11, 1453
10. A. S. K. Hashmi, C. Hubbert, Angew. Chem. 2010, 122, 1026
11. Angew. Chem. Int. Ed. 2010, 49, 1010
12. J. T. Binder, B. Crone, T. T. Haug, H. Menz, S. F. Kirsch, Org. Lett. 2008, 10, 1025
13. M. Ikeda, Y. Miyake, Y. Nishibayashi, Angew. Chem. 2010, 122, 7447
14. Angew. Chem. Int. Ed. 2010, 49, 7289.
15. Z. H. Xu, P. Daka, H. Wang, Chem. Commun. 2009, 6825
16. Z. H. Xu, P. Daka, I. Budik, H. Wang, F. Q. Bai, H. X. Zhang, Eur. J. Org. Chem. 2009, 4581
17. P. Daka, Z. H. Xu, A. Alexa, H. Wang, Chem. Commun. 2011, 47, 224.
18. D. H. Paull, C. J. Abraham, M. T. Scerba, E. Alden-Danforth, T. Lectka, Acc. Chem. Res. 2008, 41, 655
19. H. Gröger, Chem. Eur. J. 2001, 7, 5246
20. L. Y. Wu, G. Bencivenni, M. Mancinelli, A. Mazzanti, G. Bartoli, P. Melchiorre, Angew. Chem. 2009, 121, 7332
21. Angew. Chem. Int. Ed. 2009, 48, 7196
22. M. Kanai, N. Kato, E. Ichikawa, M. Shibasaki, Synlett 2005, 1491.
23. H. Pellissier, Tetrahedron 2009, 65, 2839
24. K. A. Jørgensen, Eur. J. Org. Chem. 2004, 2093
25. K. A. Jørgensen, M. Johannsen, S. Yao, H. Audrain, J. Thorhauge, Acc. Chem. Res. 1999, 32, 605
26. R. Alfini, M. Cecchi, D. Giomi, Molecules 2010, 15, 1722.
27. K. Juhl, K. A. Jørgensen, Angew. Chem. 2003, 115, 1536
28. Angew. Chem. Int. Ed. 2003, 42, 1498
29. Y. Zhao, X. J. Wang, J. T. Liu, Synlett 2008, 1017
30. S. Samanta, J. Krause, T. Mandal, C. G. Zhao, Org. Lett. 2007, 9, 2745
31. H. X. Xie, L. S. Zu, H. R. Oueis, H. L. J. Wang, W. Wang, Org. Lett. 2008, 10, 1923
32. B. Han, Z. Q. He, J. L. Li, R. Li, K. Jiang, T. Y. Liu, Y. C. Chen, Angew. Chem. 2009, 121, 5582
33. Angew. Chem. Int. Ed. 2009, 48, 5474
34. B. Han, J. L. Li, C. Ma, S. J. Zhang, Y. C. Chen, Angew. Chem. 2008, 120, 10119
35. Angew. Chem. Int. Ed. 2008, 47, 9971.
36. HDA reaction of enamide derived from cyclic ketones:, F. Gallier, H. Hussain, A. Martel, A. Kirschning, G. Dujardin, Org. Lett. 2009, 11, 3060.
37. Organocatalytic reaction of cyclic ketone with enone leading to aldol product:, C. Zheng, Y. Wu, X. Wang, G. Zhao, Adv. Synth. Catal. 2008, 350, 2690.
38. Organocatalytic reaction of cyclic ketone with enone leading to formal [3+3] annulation product:, C. L. Cao, X. L. Sun, Y. B. Kang, Y. Tang, Org. Lett. 2007, 9, 4151.
39. For reviews, see ref. [4] and a) G. Desimoni, G. Faita, K. A. Jorgensen, Chem. Rev. 2006, 106, 3561
40. J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325; For representative examples, see
41. K. Gademann, D. E. Chavez, E. N. Jacobsen, Angew. Chem. 2002, 114, 3185
42. Angew. Chem. Int. Ed. 2002, 41, 3059
43. D. A. Evans, J. S. Johnson, E. J. Olhava, J. Am. Chem. Soc. 2000, 122, 1635
44. H. Audrain, J. Thorhauge, R. G. Hazell, K. A. Jorgensen, J. Org. Chem. 2000, 65, 4487
45. W. Zhuang, J. Thorhauge, K. A. Jorgensen, Chem. Commun. 2000, 459
46. G. Desimoni, G. Faita, M. Toscanini, M. Boiocchi, Chem. Eur. J. 2007, 13, 9478
47. G. Desimoni, G. Faita, M. Mella, F. Piccinini, M. Toscanini, Eur. J. Org. Chem. 2007, 1529
48. D. H. Paull, E. Alden-Danforth, J. Wolfer, C. Dogo-Isonagie, C. J. Abraham, T. Lectka, J. Org. Chem. 2007, 72, 5380
49. F. Gohier, K. Bouhadjera, D. Faye, C. Gaulon, V. Maisonneuve, G. Dujardin, R. Dhal, Org. Lett. 2007, 9, 211.
50. The minor diastereomer of the HDA products was identified as an epimer (at C8a) of the endo product that resulted from the hydrolysis in the last step (refer to Scheme 1). See the Supporting Information for relevant experiments and NMR spectroscopy.
51. 2. CCDC 806477 (4g) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.