Synthesis of an amino-functionalized ansa-zirconocene by intramolecular photochemical enamine [2+2]Cycloaddition

Organometallics

Volumn 28, Issue 15, 2009, Pages 4513-4518

  Tumay, Tülay Ash ^a   Kehr, Gerald ^a   Fröhlich, Roland ^a   Erker, Gerhard ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

[2 + 2] CYCLOADDITION; BIS(ENAMINO-CP); CONTROLLED REACTION CONDITIONS; ENAMINES; FRACTIONAL CRYSTALLIZATION; FUNCTIONALIZED; MANNICH CONDENSATION; MINOR COMPONENTS; PHOTOPRODUCTS; PYREX FILTER; X- RAY DIFFRACTION; ZIRCONIUM TETRACHLORIDE; ZIRCONOCENE COMPLEXES; ZIRCONOCENES;

ACIDS; AMINES; CYCLOADDITION; PARAFFIN WAXES; PHOTOLYSIS; ZIRCONIUM; ZIRCONIUM COMPOUNDS;

LITHIUM;

EID: 68149124384     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9003576     Document Type: Article

References (60)

1. (a) Marks, T. J. Acc. Chem. Res. 1992, 25, 57-65.
2. (b) Brintzinger, H.-H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem. 1995, 107, 1255-1283;
3. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143-1170.
4. (c) Kaminsky, W. J. Chem. Soc., Dalton Trans. 1998, 1413-1418.
5. (d) Alt, H. G.; Samuel, E. Chem. Soc. Rev. 1998, 27, 323-329.
6. (e) Alt, H. G.; Köppl, A. Chem. Rev. 2000, 100, 1205-1221.
7. (f) Erker, G. Acc. Chem. Res. 2001, 34, 309-317.
8. (g) Erker, G. Chem. Commun. 2003, 1469-1476.
9. (a) Erker, G.; Kehr, G.; Fröhlich, R. J. Organomet. Chem. 2004, 689, 1402-1412.
10. (b) Erker, G. Polyhedron 2005, 24, 1289-1297.
11. (c) Erker, G.; Kehr, G.; Fröhlich, R. Coord. Chem. Rev. 2006, 250, 36-46.
12. (d) Erker, G. Macromol. Symp. 2006, 236, 1-13.
13. (a) Hüerländer, D.; Kleigrewe, N.; Kehr, G.; Erker, G.; Fröhlich, R. Eur. J. Inorg. Chem. 2002, 2633-2642.
14. (b) Ogasawara, M.; Nagano, T.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 9068-9069.
15. (c) Sierra, J. C.; Hüerländer, D.; Hill, M.; Kehr, G.; Erker, G.; Fröhlich, R. Chem. Eur. J. 2003, 9, 3618-3622.
16. (d) Kuwabara, J.; Takeuchi, D.; Osakada, K. Organo-metallics 2005, 24, 2705-2712.
17. (a) Knüppel, S.; Erker, G.; Fröhlich, R. Angew. Chem. 1999, 111, 2048-2051;
18. Angew. Chem., Int. Ed. 1999, 38, 1923-1926.
19. (b) Knüppel, S.; Wang, C.; Kehr, G.; Fröhlich, R.; Erker, G. J. Organomet. Chem. 2005, 690, 14-32.
20. Venne-Dunker, S.; Kehr, G.; Fröhlich, R.; Erker, G. Organome-tallics 2003, 22, 948-958.
21. Bai, S.-D.; Wei, X.-H.; Guo, J.-P.; Liu, D.-S.; Zhou, Z.-Y. Angew. Chem. 1999, 111, 2051-2054;
22. Angew. Chem., Int. Ed. 1999, 38, 1926-1928.
23. See for comparison: (a) Knüppel, S.; Fröhlich, R.; Erker, G. J. Organomet. Chem. 1999, 586, 218-222.
24. (b) Knüppel, S.; Fröhlich, R.; Erker, G. J. Organomet. Chem. 2000, 595, 308-312.
25. (c) Liptau, P.; Knüppel, S.; Kehr, G.; Kataeva, O.; Fröhlich, R.; Erker, G. J. Organomet. Chem. 2001, 637-639, 621-630.
26. (a) Erker, G.; Wilker, S.; Krüger, C.; Goddard, R. J. Am. Chem. Soc. 1992, 114, 10983-10984.
27. (b) Erker, G.; Wilker, S.; Krüger, C.; Nolte, M. Organometallics 1993, 12, 2140-2151.
28. Paradies, J.; Kehr, G.; Fröhlich, R.; Erker, G. Proc. Natl. Acad. Sci. 2006, 103, 15333-15337.
29. Erker, G.; Greger, I. Unpublished results.
30. For related examples see:
31. (a) Nie, W.-L.; Erker, G.; Kehr, G.; Fröhlich, R. Angew. Chem. 2004, 116, 313-317;
32. Angew. Chem., Int. Ed. 2004, 43, 310-313.
33. (b) Chen, L.; Nie, W.-L.; Paradies, J.; Kehr, G.; Fröhlich, R.; Wedeking, K.; Erker, G. Organometallics 2006, 25, 5333-5344.
34. (c) Paradies, J.; Erker, G.; Fröhlich, R. Angew. Chem. 2006, 118, 3150-3153;
35. Angew. Chem., Int. Ed. 2006, 45, 3079-3082.
36. (d)Paradies, J.; Greger, I.; Kehr, G.; Erker, G.; Bergander, K.; Fröhlich, R. Angew. Chem. 2006, 118, 7792-7795;
37. Angew. Chem., Int. Ed. 2006, 45, 1630-1633.
38. (e) Paradies, J.; Fröhlich, R.; Kehr, G.; Erker, G. Organometallics 2006, 25, 3920-3925.
39. For organic examples of photochemical enamine cycloaddition reactions see for example: (a) Winkler, J. D.; Muller, C. L.; Scott, R. D. J. Am. Chem. Soc. 1988, 110, 4831-4832.
40. (b) Amougay, A.; Pete, J.-P.; Piva, O. Tetrahedron Lett. 1992, 33, 7347-7350.
41. (c) Johnson, B. L.; Kitahara, Y.; Weakley, T. J. R.; Keana, J. F. W. Tetrahedron Lett. 1993, 34, 5555-5558.
42. (d) Oldroyd, D. L.; Payne, N. C.; Vittal, J. J.; Weedon, A. C.; Zhang, B. Tetrahedron Lett. 1993, 34, 1087-1090.
43. (e) Carell, T.; Epple, R.; Gramlich, V. Helv. Chim. Acta 1997, 80, 2191-2203.
44. (f ) Itoh, K.; Fujimoto, M.; Hashimoto, M. New J. Chem. 2002, 26, 1070-1075.
45. (g) White, J. D.; Ihle, D. C. Org. Lett. 2006, 8, 1081-1084.
46. (a) Hafner, K.; Vöpel, K. H.; Ploss, G.; König, C. Liebigs Ann. Chem. 1963, 661, 52-75.
47. (b) Hafner, K.; Schulz, G.; Wagner, K. Liebigs Ann. Chem. 1964, 678, 39-53.
48. (c) Hafner, K.; Vöpel, K. H.; Ploss, G.; König, C. Org. Synth. 1967, 47, 52-54.
49. Kunz, K.; Pflug, J.; Bertuleit, A.; Fröhlich, R.; Wegelius, E.; Erker, G.; Würthwein, E.-U. Organometallics 2000, 19, 4208-4216.
50. See for a comparison: Eliel, E. L.; Wilen, S. H.; Doyle, M. P. Basic Organic Stereochemistry; Wiley-Interscience: New York, 2001.
51. (a) Erker, G.; Mühlenbernd, T.; Benn, R.; Rufinska, A.; Tsay, Y.-H.; Krüger, C. Angew. Chem. 1985, 97, 336-337;
52. Angew. Chem., Int. Ed. Engl. 1985, 24, 321-323.
53. (b) Erker, G.; Nolte, R.; Tainturier, G.; Rheingold, A. Organometallics 1989, 8,454-460.
54. (c) Erker, G.; Nolte, R.; rüger, C.; Schlund, R.; Benn, R.; Grondey, H.; Mynott, R. J. Organomet. Chem. 1989, 364, 119-132.
55. (d) Erker, G.; Aulbach, M.; Knickmeier, M.; Wingbermühle, D.; Krüger, C.; Nolte, M.; Werner, S. J. Am. Chem. Soc. 1993, 115, 4590-4601.
56. (e) Knickmeier, M.; Erker, G.; Fox, T. J. Am. Chem. Soc. 1996, 118, 9623-9630.
57. (f ) Jödicke, T.; Menges, F.; Kehr, G.; Erker, G.; Höweler, U.; Fröhlich, R. Eur. J. Inorg. Chem. 2001, 2097-2106.
58. (a) Cohen, M. D.; Schmidt, G. M. J. J. Chem. Soc. 1964, 1996-2000.
59. (b) Schmidt, G. M. J. J. Chem. Soc. 1964, 2014-2021.
60. (c) Bregman, J.; Osaki, K.; Schmidt, G. M. J.; Sonntag, F. I. J. Chem. Soc. 1964, 2021-2030.