Ferrocenylphosphines as new catalysts for Baylis-Hillman reactions

Journal of Organic Chemistry

Volumn 70, Issue 24, 2005, Pages 10175-10177

  Pereira, Susana Isabel ^a   Adrio, Javier ^a   Silva, Artur M S ^b   Carretero, Juan Carlos ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b UNIVERSITY OF AVEIRO   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYST SELECTIVITY; PHOSPHORUS COMPOUNDS; REACTION KINETICS;

BAYLIS-HILLMAN REACTIONS; ENANTIOSELECTIVITY; FERROCENYLPHOSPHINES;

CATALYSTS;

ACRYLIC ACID DERIVATIVE; ALDEHYDE; BENZALDEHYDE; BENZYL ACRYLATE; FERROCENE DERIVATIVE; FERROCENYLDIETHYLPHOSPHINE; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; REACTION TIME; SYNTHESIS;

EID: 28044437774     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051701n     Document Type: Article

References (46)

1. For recent reviews, see: (a) Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035.
2. (b) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
3. (c) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
4. (d) Ciganek, E. In Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1997; Vol. 51, p 201.
5. Fort, Y.; Berthe, M. C.; Caubere, P. Tetrahedron 1992, 48, 6371.
6. (a) Cai, J.; Zhou, Z.; Zhao, G.; Tang, C. Org. Lett. 2002, 4, 4723.
7. (b) Auge, J.; Lubin, N.; Lubineau, A. Tetrahedron Lett. 1994, 35, 7947.
8. (c) Basavaiah, D.; Sarma, P. K. S. Synth. Commun. 1990, 20, 5019.
9. Kawamura, K.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 1539-1542.
10. (a) Aggarwal, V. K.; Mereu, A.; Tarver, G. J.; McCague, R. J. Org. Chem. 1998, 63, 7183.
11. (b) Pei, W.; Wei, H.-X.; Li, G. Chem. Commun. 2002, 1856.
12. (c) Yang, K.; Lee, W.; Pan, J.; Chen, K. J. Org. Chem. 2003, 68, 915.
13. (d) You, J.; Xu, J.; Verkade, J. G. Angew. Chem., Int. Ed. 2003, 42, 5054.
14. (a) Rosa, J. N.; Afonso, C. A. M.; Santos, A. G. Tetrahedron 2001, 57, 4189.
15. (b) Aggarwal, V. K.; Emme, I.; Mereu, A. Chem. Commun. 2002, 1612.
16. (c) Pégot, B.; Vo-Thanh, G.; Gori, D.; Loupy, A. Tetrahedron Lett. 2004, 45, 6425.
17. Hayashi, Y.; Okado, K.; Ashimine, I.; Shoji, M. Tetrahedron Lett. 2002, 43, 8683.
18. Coelho, F.; Almeida, P. A.; Veronese, D.; Mateus, C. R.; Silva Lopes, E. C.; Rossi, R. C.; Silveira, G. P. C.; Pavam, C. H. Tetrahedron 2002, 58, 7437.
19. Kundu, M. K.; Mukherjee, S. B.; Balu, N.; Padmakumar, R.; Bhat, S. V. Synlett. 1994, 444.
20. (a) Rauhut, M. M.; Currier, H. U. S. Patent, 1963, 3074999; Chem. Abstr. 1963, 58, 11224a.
21. (b) Rafel, S.; Leahy, J. W. J. Org. Chem. 1997, 62, 1521 and references therein.
22. (a) Henderson, W. A.; Buckler, S. A. J. Am. Chem. Soc. 1960, 82, 5794.
23. (b) Person, R. G.; Sobel, H.; Songtad, J. J. Am. Chem. Soc. 1968, 90, 319.
24. (c) Rahman, M. M.; Liu, H.-Y.; Eriks, K.; Prock, A.; Giering, W. P. Organometallics 1989, 8, 3.
25. Netherton, R. M.; Fu, G. C. Org. Lett. 2001, 3, 4295.
26. Colacot, T. J. Chem. Rev. 2003, 103, 3101.
27. (a) Ahrendt, K. A.; Bergman R. G.; Ellman J. A. Org. Lett. 2003, 5, 1301.
28. (b) Guillaneux, D.; Kagan, H. J. Org. Chem. 1995, 60, 2502.
29. 2O afforded lower yields.
30. For a review, see: Langer, P. Angew. Chem., Int. Ed. 2000, 39, 3049.
31. (a) Brzezinski, L. J.; Rafel, S.; Leahy, J. J. Am. Chem. Soc. 1997, 119, 4317.
32. (b) Yang, K.-S.; Chen, K. Org. Lett. 2000, 2, 729.
33. (c) W. Krishna, P. R.; Sachwani, R.; Kannan, V. Chem. Commun. 2004, 2580.
34. (a) Shi, M.; Jiang, J.-K.; Tetrahedron: Asymmetry 2002, 13, 1951.
35. (b) Kawahara, S.; Nakano, A.; Esumi, T.; Iwabuchi, Y.; Hatakeyama, S. Org. Lett. 2003, 5, 3103.
36. (a) McDougal, N. T.; Schaus, S. E. J. Am. Chem. Soc. 2003, 125, 12094.
37. (b) McDougal, N. T.; Trvellini, W. L.; Rodgen, S. A.; Kliman, L. T.; Schaus, S. Adv. Synth. Catal. 2004, 346, 1231.
38. (a) Roth, F.; Crygak, P.; Fráter, G. Tetrahedron Lett. 1992, 33, 1045.
39. (b) Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. Chem. Commun. 1998, 1271.
40. (b) Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. J. Org. Chem. 2000, 65, 3489.
41. The best results to date using chiral phosphines were obtained in the aza-Baylis-Hillman reaction of N-sulfonilated imines with methyl vinyl ketone using 2′-diphenylphosphanyl[1,1′]binaphthalenyl2-ol as catalyst (76-94% ee). Shi, M.; Chen L.-H. Chem. Commun. 2003. 1310.
42. Although, to the best of our knowledge, there is not cases of the utilization of chiral ferrocene phosphines in the Baylis-Hillman reaction, an example of its utilization in the aza-Baylis-Hillman reaction has been recently described. Shi, M.; Chen L.-H. Li, C.-Q. J. Am. Chem. Soc. 2005, 127, 3790.
43. (a) Priego, J.; García Mancheño, O.; Cabrera, S.; Gómez-Arrayás, R.; Llamas T. Carretero, J. C. Chem. Commun. 2002, 2512.
44. (b) García Mancheño, O.; Priego, J.; Cabrera, S.; Gómez-Arrayás, R.; Llamas T.; Carretero, J. C. J. Org. Chem. 2003, 68, 3679.
45. (c) García Mancheño O.; Gómez-Arrayás, R.; Carretero, J. C. J. Am. Chem. Soc. 2004. 125, 456.
46. (d) Cabrera, S.; Gómez-Arrayás, R.; Carretero, J. C. Angew. Chem., Int. Ed. 2004, 43, 3944.