Palladium-catalyzed asymmetric 1,4-addition of diarylphosphines to nitroalkenes for the synthesis of chiral P,N-compounds

Advanced Synthesis and Catalysis

Volumn 354, Issue 16, 2012, Pages 3122-3126

  Feng, Jian Jun ^b   Huang, Miao ^b   Lin, Zi Qi ^a   Duan, Wei Liang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

1,4 addition; asymmetric hydrophosphination; diarylphosphines; nitroalkenes; pincer palladium catalysts

Indexed keywords

EID: 84869043658     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201200133     Document Type: Review

References (59)

1. Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications, Vols. 1-3, (Ed.:, A. Börner,), Wiley-VCH, Weinheim, 2008.
2. For a review of 1,4-addition reactions of phosphorus nucleophiles to electron-deficient olefins, see:, D. Enders, A. Saint-Dizier, M.-I. Lannou, A. Lenzen, Eur. J. Org. Chem. 2006, 29.
3. D. S. Glueck, Chem. Eur. J. 2008, 14, 7108
4. D. S. Glueck, Synlett 2007, 2627
5. J. S. Harvey, V. Gouverneur, Chem. Commun. 2010, 7477
6. D. Zhao, R. Wang, Chem. Soc. Rev. 2012, 41, 2095. For leading examples, see
7. I. Kovacik, D. K. Wicht, N. S. Grewal, D. S. Glueck, C. D. Incarvito, I. A. Guzei, A. L. Rheingold, Organometallics 2000, 19, 950
8. C. Scriban, I. Kovacik, D. S. Glueck, Organometallics 2005, 24, 4871
9. C. Scriban, D. S. Glueck, L. N. Zakharov, W. S. Kassel, A. G. DiPasquale, J. A. Golen, A. L. Rheingold, Organometallics 2006, 25, 5757
10. A. D. Sadow, I. Haller, L. Fadini, A. Togni, J. Am. Chem. Soc. 2004, 126, 14704
11. A. D. Sadow, A. Togni, J. Am. Chem. Soc. 2005, 127, 17012
12. P. Butti, R. Rochat, A. D. Sadow, A. Togni, Angew. Chem. 2008, 120, 4956
13. Angew. Chem. Int. Ed. 2008, 47, 4878
14. J. R. Moncarz, N. F. Laritcheva, D. S. Glueck, J. Am. Chem. Soc. 2002, 124, 13356
15. N. F. Blank, J. R. Moncarz, T. J. Brunker, C. Scriban, B. J. Anderson, O. Amir, D. S. Glueck, L. N. Zakharov, J. A. Golen, C. D. Incarvito, A. L. Rheingold, J. Am. Chem. Soc. 2007, 129, 6847
16. V. S. Chan, R. G. Bergman, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 15122
17. V. S. Chan, I. C. Stewart, R. G. Bergman, F. D. Toste, J. Am. Chem. Soc. 2006, 128, 2786
18. C. Scriban, D. S. Glueck, J. Am. Chem. Soc. 2006, 128, 2788
19. V. S. Chan, M. Chiu, R. G. Bergman, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 6021
20. L. Hong, W. Sun, C. Liu, D. Zhao, R. Wang, Chem. Commun. 2010, 2856
21. W. Sun, L. Hong, C. Liu, R. Wang, Org. Lett. 2010, 12, 3914
22. M. Nielsen, C. B. Jacobsen, K. A. Jørgensen, Angew. Chem. 2011, 123, 3269
23. Angew. Chem. Int. Ed. 2011, 50, 3211.
24. A. Carlone, G. Bartoli, M. Bosco, L. Sambri, P. Melchiorre, Angew. Chem. 2007, 119, 4588
25. Angew. Chem. Int. Ed. 2007, 46, 4504
26. I. Ibrahem, R. Rios, J. Vesely, P. Hammar, L. Eriksson, F. Himo, A. Córdova, Angew. Chem. 2007, 119, 4591
27. Angew. Chem. Int. Ed. 2007, 46, 4507
28. I. Ibrahem, P. Hammar, J. Vesely, R. Rios, L. Eriksson, A. Córdova, Adv. Synth. Catal. 2008, 350, 1875
29. J.-J. Feng, X.-F. Chen, M. Shi, W.-L. Duan, J. Am. Chem. Soc. 2010, 132, 5562
30. D. Zhao, L. Mao, D. Yang, R. Wang, J. Org. Chem. 2010, 75, 6756
31. D. Zhao, L. Mao, Y. Wang, D. Yang, Q. Zhang, R. Wang, Org. Lett. 2010, 12. 1880
32. S. Wen, L. Li, H. Wu, F. Yu, X. Liang, J. Ye, Chem. Commun. 2010, 4806
33. Y. Huang, S. A. Pullarkat, L. Li, P.-H. Leung, Chem. Commun. 2010, 6950
34. A. Russo, A. Lattanzi, Eur. J. Org. Chem. 2010, 6736
35. M.-J. Yang, Y.-J. Liu, J.-F. Gong, M.-P. Song, Organometallics 2011, 30, 3793
36. D. Du, W.-L. Duan, Chem. Commun. 2011, 47, 11101
37. X. Luo, Z. Zhou, X. Li, X. Liang, J. Ye, RSC Advances 2011, 1, 698
38. Y.-R. Chen, W.-L. Duan, Org. Lett. 2011, 13. 5824
39. Y. Huang, R. J. Chew, Y. Li, S. A. Pullarkat, P.-H. Leung, Org. Lett. 2011, 13. 5862.
40. For a review on asymmetric 1,4-addition to nitroalkenes, see:, O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877.
41. K. Sumi, T. Ikariya, R. Noyori, Can. J. Chem. 2000, 78, 697
42. R. Guo, A. J. Lough, R. H. Morris, D. Song, Organometallics 2004, 23, 5524
43. R. Guo, R. H. Morris, D. Song, J. Am. Chem. Soc. 2005, 127, 516
44. M. Ito, S. Kitahara, T. Ikariya, J. Am. Chem. Soc. 2005, 127, 6172
45. J.-B. Xie, J.-H. Xie, X.-Y. Liu, W.-L. Kong, S. Li, Q.-L. Zhou, J. Am. Chem. Soc. 2010, 132, 4538
46. J.-B. Xie, J.-H. Xie, X.-Y. Liu, Q.-Q. Zhang, Q.-L. Zhou, Chem. Asian J. 2011, 6, 899.
47. S. Dalili, A. Caiazzo, A. K. Yudin, J. Organomet. Chem. 2004, 689, 3604
48. Y.-Q. Fang, E. N. Jacobsen, J. Am. Chem. Soc. 2008, 130, 5660
49. K. Yuan, L. Zhang, H.-L. Song, Y. Hu, X.-Y. Wu, Tetrahedron Lett. 2008, 49, 6262
50. H.-L. Song, K. Yuan, X.-Y. Wu, Chem. Commun. 2011, 1012.
51. G. Bartoli, M. Bosco, A. Carlone, M. Locatelli, A. Mazzanti, L. Sambri, P. Melchiorre, Chem. Commun. 2007, 722.
52. X. Fu, Z. Jiang, C.-H. Tan, Chem. Commun. 2007, 5058
53. B. Cho, C.-H. Tan, M. W. Wong, Org. Biomol. Chem. 2011, 9, 4550.
54. M. Albrecht, G. van Koten, Angew. Chem. 2001, 113, 3866
55. Angew. Chem. Int. Ed. 2001, 40, 3750
56. N. Selander, K. J. Szabó, Chem. Rev. 2011, 111, 2048.
57. J. M. Longmire, X. Zhang, Tetrahedron Lett. 1997, 38, 1725
58. J. M. Longmire, X. Zhang, M. Shang, Organometallics 1998, 17, 4374.
59. A. Caiazzo, S. Dalili, A. K. Yudin, Org. Lett. 2002, 4. 2597.