Activated alkene dependent one-pot, three-component aza-Morita-Baylis- Hillman reaction of ferrocenealdehyde: Synthesis of highly functionalized diverse ferrocene derivatives

Organic Letters

Volumn 13, Issue 7, 2011, Pages 1590-1593

  Madhavan, Suchithra ^a   Shanmugam, Ponnusamy ^b  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b CENTRAL LEATHER RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE; FERROCENE; FERROUS ION;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; ALKENES; FERROUS COMPOUNDS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 79953207723     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200215d     Document Type: Article

References (61)

1. Kealy, T. J.; Pauson, P. L. Nature 1951, 168, 1039
2. Togni, A.; Hayashi, T., Eds. Ferrocenes: Homogenous Catalysis. Organic Synthesis, Materials Science; VCH: Weinheim, Germany, 1995.
3. Togni, A.; Haltermann, R. L., Eds. Metallocenes; VCH: Weinheim, Germany, 1998.
4. Stepnicka, P., Ed. Ferrocenes: Ligands, Materials and Biomolecules; John Wiley & Sons, Inc.: New York, 2008; p 39.
5. Sudhir, V. S.; Baig, N. B. R.; Chandrasekharan, S. Eur. J. Org. Chem. 2009, 5365
6. Sierra, M. A.; Rodríguez-Fernández, M.; Casarrubios, L.; Gómez-Gallego, M.; Allen, C. P.; Mancheño, M. J. Dalton Trans. 2009, 39, 8399
7. James, P.; Neudorfl, J.; Jesse, P.; Prokop, A.; Schmalz, H.-G. Org. Lett. 2006, 8, 2763
8. Tauchman, J.; Stepnicka, P. Inorg. Commun. 2010, 13, 149
9. Garcia, A.; Insuasty, B.; Herranz, M. A.; Martinez-Alvarez, R.; Martin, N. Org. Lett. 2009, 11, 5398
10. Chebny, V. J.; Dhar, D.; Lindeman, S. V.; Rathore, R. Org. Lett. 2006, 8, 5041
11. Li, Q.; Ding, C.-H.; Hou, X.-L.; Dai, L.-X. Org. Lett. 2010, 12, 1080
12. Marquard, S. L.; Rosenfeld, D. C.; Hartwig, J. F. Angew. Chem., Int. Ed. 2010, 49, 793
13. Thomas, J. C. Chem. Rev. 2003, 103, 3101
14. Dai, L.-X.; Tu, T.; You, S.-L.; Deng, W.-P.; Hou, X.-L. Acc. Chem. Res. 2003, 36, 659
15. Arrayas, R. G.; Adrio, J.; Carretero, J. C. Angew. Chem., Int. Ed. 2006, 45, 7674
16. Atkinson, R. C. J.; Gibson, V. C.; Long, N. J. Chem. Soc. Rev. 2004, 33, 313
17. Wang, W.; Sun, H.; Kaifer, A. E. Org. Lett. 2007, 9, 2657
18. Moriuchi, T.; Hirao, T. Chem. Soc. Rev. 2004, 33, 294
19. Even, M.; Heinrich, B.; Guillon, D.; Guldi, D. M.; Prato, M.; Deschenaux, R. Chem.-Eur. J. 2001, 7, 2595
20. Li, Z.; Godsell, J. F.; O'Byrne, J. P.; Petkov, N.; Morris, M. A.; Roy, S.; Holmes, J. D. J. Am. Chem. Soc. 2010, 132, 12540
21. Boulas, P. L.; Gomez-Kaifer, M.; Echegoyen, L. Angew. Chem., Int. Ed. 1998, 37, 216
22. van Staveren, D. R.; Metzler-Nolte, N. Chem. Rev. 2004, 104, 5931
23. Kraatz, H.-B. J. Inorg. Organomet. Polym. Mater. 2005, 15, 83
24. Chowdhury, S.; Schatte, G.; Kraatz, H.-B. Angew. Chem., Int. Ed. 2006, 45, 6882
25. Drexler, C.; Milne, M.; Morgan, E.; Jennings, M.; Kraatz, H.-B. Dalton Trans. 2009, 4370
26. Hamels, D.; Dansette, P. M.; Hillard, E. A.; Top, S.; Vessieres, A.; Herson, P.; Jaouen, G.; Mansuy, D. Angew. Chem., Int. Ed. 2009, 48, 9124
27. Schatzschneider, U.; Metzler-Nolte, N. Angew. Chem., Int. Ed. 2006, 45, 1504
28. Balemans, W.; Lounis, N.; Gillisen, R.; Guillemont, J.; Simmen, K.; Andries, K.; Koul, A. Nature 2010, 463, E3
29. Fache, F.; Schulz, E.; Tommasino, M. L.; Lemaire, M. Chem. Rev. 2000, 100, 2159
30. Blaser, H.-U.; Malan, C.; Pugin, B.; Spindler, F.; Steiner, H.; Studer, M. Adv. Synth. Catal. 2003, 345, 103
31. Moriuchi, T.; Hirao, T. Acc. Chem. Res. 2010, 43, 1040
32. Kirin, S. I.; Kraatz, H.-B.; Metzler-Nolte, N. Chem. Soc. Rev. 2006, 35, 348
33. Declerck, V.; Martinez, J.; Lamaty, F. Chem. Rev. 2009, 109, 1
34. Shi, Y.-L.; Shi, M. Eur. J. Org. Chem. 2007, 2905
35. Ma, G.-N.; Jiang, J.-J.; Shi, M.; Wei, Y. Chem. Commun. 2009, 5946
36. Batra, S.; Singh, V. Tetrahedron 2008, 64, 4511
37. Shi, Y.-L.; Shi, M. Org. Biomol. Chem. 2007, 5, 1499
38. Basavaiah, D.; Rao, A. J.; Satayanarayana, T. Chem. Rev. 2003, 103, 811
39. Masson, G.; Housseman, C.; Zhu, J. Angew. Chem., Int. Ed. 2007, 46, 4614
40. Bretenshaw, S.; Kahn, M. Tetrahedron Lett. 1989, 30, 273
41. Balan, D.; Adolfsson, H. J. Org. Chem. 2001, 66, 6498
42. Balan, D.; Adolfsson, H. J. Org. Chem. 2002, 67, 2329
43. Balan, D.; Adolfsson, H. Tetrahedron Lett. 2003, 44, 2521
44. Selvakumar, K.; Vaithiyanathan, V.; Shanmugam, P. Chem. Commun. 2010, 46, 2826
45. Viswambharan, B.; Selvakumar, K.; Madhavan, S.; Shanmugam, P. Org. Lett. 2010, 12, 2108
46. Shanmugam, P.; Vaithiyanathan, V.; Viswambharan, B.; Madhavan, S. Tetrahedron Lett. 2007, 48, 9190
47. Shanmugam, P.; Madhavan, S.; Selvakumar, K.; Vaithiyanathan, V.; Viswambharan, B. Tetrahedron Lett. 2009, 50, 2213
48. Cheng, R. P.; Gellman, S. H.; Degrado, W. F. Chem. Rev. 2001, 101, 3219
49. Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893
50. Lelais, G.; Seebach, D. Biopolymers 2004, 76, 206
51. Adamczyk, M.; Reddy, R. E.; Rege, S. D. Synth. Commun. 2000, 30, 1389
52. Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Soc. Rev. 2007, 36, 1581
53. Basavaiah, D.; Rao, K. V.; Reddy, R. J. Chem. Rev. 2010, 110, 5447
54. Also it is to be noted that during our investigation in MBH adduct formation, we found both ferrocene mono and bis aldehydes were reluctant to form corresponding adducts with Michael acceptors like acrylates, methyl vinyl ketone, phenyl vinyl sulfones, amides, cyclic enones, allenes, etc.
55. 3 and DABCO, see: Shi, M.; Xu, Y.-L. Eur. J. Org. Chem. 2002, 696
56. The crystallographic coordinates have been deposited with the Cambridge Crystallographic Data Centre; deposition no. 788036. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Rd., Cambridge CB2 1EZ, UK or via www.ccdc.cam.ac.uk/conts/retrieving.html.
57. Cabrera, S.; Aleman, J.; Bolze, P.; Bertelsen, S.; Jorgensen, K. A. Angew. Chem., Int. Ed. 2008, 47, 121
58. Handa, S.; Kachala, M. S.; Lowe, S. R. Tetrahedron Lett. 2004, 45, 253
59. Vesely, J.; Dziedzic, P.; Cordova, A. Tetrahedron Lett. 2007, 48, 6900
60. Shi, M.; Jiang, J.-K.; Li, C.-Q. Tetrahedron Lett. 2002, 43, 127
61. Utsumi, N.; Zhang, H.; Tanaka, F.; Barbas, C. F. Angew. Chem., Int. Ed. 2007, 46, 1878