Catalytic asymmetric hydrophosphinylation of α,β-unsaturated N -acylpyrroles: Application of dialkyl phosphine oxides in enantioselective synthesis of chiral phosphine oxides or phosphines

Organic Letters

Volumn 12, Issue 8, 2010, Pages 1880-1882

  Zhao, Depeng ^a   Mao, Lijuan ^a   Wang, Yuan ^a   Yang, Dongxu ^a   Zhang, Quanliang ^a   Wang, Rui ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

OXIDE; PHOSPHINE; PHOSPHINE DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; ENZYME SPECIFICITY; STEREOISOMERISM;

CATALYSIS; OXIDES; PHOSPHINES; PYRROLES; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 77951182952     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100504h     Document Type: Article

References (42)

1. For reviews, see
2. Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029-3069
3. Hayashi, T. Acc. Chem. Res. 2000, 33, 354-362
4. The role of phosphonates in living systems; Hildebrand, P. L., Ed.; CRC Press: Boca Raton, FL, 1983.
5. Engel, R. Chem. Rev. 1977, 77, 349-367
6. Romanenko, V. D.; Kukhar, V. P. Chem. Rev. 2006, 106, 3868-3935
7. For reviews, see
8. Ordóñez, M.; Rojas-Cabrera, H.; Cativiela, C. Tetrahedron 2009, 65, 17-49
9. Ma, J. A. Chem. Soc. Rev. 2006, 35, 630-636
10. Merino, P.; Marqués-López, E.; Herrera, R. P. Adv. Synth. Catal. 2008, 350, 1195-1208
11. Gröger, H.; Hammer, B. Chem. - Eur. J. 2000, 6, 943-948
12. Enders, D.; Saint-Dizier, A.; Lannou, M.-I.; Lenzen, A. Eur. J. Org. Chem. 2006, 2, 9-49
13. Sadow, A. D.; Haller, I.; Fadini, L.; Togni, A. J. Am. Chem. Soc. 2004, 126, 14704-14705
14. Sadow, A. D.; Togni, A. J. Am. Chem. Soc. 2005, 127, 17012-17024
15. Ibrahem, I.; Rios, R.; Vesely, J.; Hammar, P.; Eriksson, L.; Himo, F.; Córdova, A. Angew. Chem., Int. Ed. 2007, 46, 4507-4510
16. Carlone, A.; Bartoli, G.; Bosco, M.; Sambri, L.; Melchiorre, P. Angew. Chem., Int. Ed. 2007, 46, 4504-4506
17. Bartoli, G.; Bosco, M.; Carlone, A.; Locatelli, M.; Mazzanti, A.; Sambri, L.; Melchiorre, P. Chem. Commun. 2007, 722-724
18. Yamakoshi, K.; Harwood, S. J.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 2565-2568
19. Fu, X.; Loh, W.-T.; Zhang, Y.; Chen, T.; Ma, T.; Liu, H.; Wang, J.; Tan, C.-H. Angew. Chem., Int. Ed. 2009, 48, 7387-7390
20. Leow, D.; Lin, S.; Chittimalla, S.; Fu, X.; Tan, C.-H. Angew. Chem., Int. Ed. 2008, 47, 5641-5645
21. Fu, X.; Jiang, Z.; Tan, C.-H. Chem. Commun. 2007, 5058-5060
22. Chatt, J.; Heaton, B. T. J. Chem. Soc. A 1968, 2745-2757
23. Ivanova, N. I.; Gusarova, N. K.; Nikitina, E. A.; Albanov, A. I.; Sinegovskaya, L. M.; Nikitin, M. V.; Konovalova, N. A.; Trofimov, B. A. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 7-18
24. Zhao, D.; Yuan, Y.; Chan, A. S. C.; Wang, R. Chem. - Eur. J. 2009, 15, 2738-2741
25. Zhao, D.; Wang, Y.; Mao, L.; Wang, R. Chem. - Eur. J. 2009, 15, 10983-10987
26. For details, see Figure S1 in the Supporting Information.
27. Kinoshita, T.; Okada, S.; Park, S.-R.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2003, 42, 4680-4684
28. Mita, T.; Sasaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 514-515
29. Yamagiwa, N.; Qin, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 13419-13427
30. Evans, D. A.; Borg, G.; Scheidt, K. A. Angew. Chem., Int. Ed. 2002, 41, 3188-3191
31. For recent examples of the bis-ProPhenol in asymmetric catalysis
32. Trost, B. M.; Malhotra, S.; Fried, B. A. J. Am. Chem. Soc. 2009, 131, 1674-1675
33. Trost, B. M.; Hitce, J. J. Am. Chem. Soc. 2009, 131, 4572-4573
34. Trost, B. M.; Malhotra, S.; Mino, T.; Rajapaksa, N. S. Chem. - Eur. J. 2008, 14, 7648-7657
35. Trost, B. M.; Muller, C. J. Am. Chem. Soc. 2008, 130, 2438-2439
36. Trost, B. M.; Shin, S. H.; Sclafani, J. A. J. Am. Chem. Soc. 2005, 127, 8602-8603
37. Trost, B. M.; Jaratjaroonphong, J.; Reutrakul, V. J. Am. Chem. Soc. 2006, 128, 2778-2779
38. Trost, B. M.; Weiss, A. H.; von Wangelin, A. J. J. Am. Chem. Soc. 2006, 128, 8-9
39. Trost, B. M.; Lupton, D. W. Org. Lett. 2007, 9, 2023-2026. See also ref 7
40. For an excellent review on additives and cocatalysts in asymmetric catalysis, see
41. Vogl, E. M.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 1570-1577
42. Diaryl phosphine oxides are not applicable to the present catalysis, only racemic products were obtained.