Stereoselective bis-functionalizations of arene chromium tricarbonyl complexes via Brook rearrangements

Organic Letters

Volumn 2, Issue 5, 2000, Pages 717-719

  Moser, William H ^a   Endsley, Kezia E ^a   Colyer, John T ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001169944     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0056022     Document Type: Article

References (36)

1. For reviews, see: (a) Uemura, M. Adv. Met. Org. Chem. 1991, 2, 195.
2. (b) Semmelhack, M. F. In Comprehensive Organometallic Chemistry II; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: New York, 1995; Vol. 12, pp 929-1015.
3. (c) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules, 2nd ed.; University Science Books: Sausalito, 1999; Chapter 10.
4. For recent examples, see: (a) Semmelhack, M. F.; Knochel, P.; Singleton, T. Tetrahedron Lett. 1993, 34, 5051.
5. (b) Tamaka, T.; Mikamiyama, H.; Maeda, K.; Ishida, T.; In, Y.; Iwata, C. J. Chem. Soc., Chem. Commun. 1997, 2401.
6. (c) Watanabe, T.; Uemura, M. J. Chem. Soc., Chem. Commun. 1998, 871.
7. (d) Schellhaas, K.; Schmalz, H. G.; Bats, J. W. Chem. Eur. J. 1998, 4, 57.
8. (e) Horstermann, D.; Schmalz, H. G.; Kociok-Kohn, G. Tetrahedron 1999, 55, 6905.
9. For recent examples, see: (a) Uemura, M.; Miyake, R.; Nakayama, K.; Shiro, M.; Hayashi, Y. J. Org. Chem. 1993, 58, 1238.
10. (b) Sodeoka, M.; Shibasaki, M. Synthesis 1993, 643.
11. (c) Jones, G. B.; Heaton, S. B.; Chapman, B. J.; Guzel, M. Tetrahedron: Asymmetry 1997, 8, 3625.
12. (d) Pasquier, C.; Naill, S.; Pelinski, L.; Brocard, J.; Mortreux, A.; Agbossou, F. Tetrahedron: Asymmetry 1998, 9, 193.
13. (e) Malfait, S.; Pelinski, L.; Brocard, J. Tetrahedron: Asymmetry 1998, 9, 2595.
14. (f) Nelson, S. G.; Hilfiker, M. A. Org. Lett. 1999, 1, 1379.
15. (a) Kundig, E. P.; Quattropani, A. Tetrahedron Lett. 1994, 35, 3497.
16. (b) Ariffin, A.; Blake, A. J.; Ewin, R. A.; Simpkins, N. S. Tetrahedron: Asymmetry 1998, 9, 2563.
17. (c) Gibson, S. E.; O'Brien, P.; Rahimian, E.; Smith, M. H. J. Chem. Soc., Perkin Trans. 1 1999, 909.
18. For an excellent review, see: Bolm, C.; Muniz, K. Chem. Soc. Rev. 1999, 28, 51. For other representative references, see: (a) Aube, J.; Heppert, J. A.; Milligan, M. L.; Smith, M. J.; Zenk, P. J. Org. Chem. 1992, 57, 3563.
19. For an excellent review, see: Bolm, C.; Muniz, K. Chem. Soc. Rev. 1999, 28, 51. For other representative references, see: (a) Aube, J.; Heppert, J. A.; Milligan, M. L.; Smith, M. J.; Zenk, P. J. Org. Chem. 1992, 57, 3563.
20. (b) Davies, S. G.; Donohoe, T. J.; Williams, J. M. J. Pure Appl. Chem. 1992, 64, 379.
21. (c) Kondo, Y.; Green, J. R.; Ho, J. J. Org. Chem. 1993, 58, 6182.
22. (d) Davies, S. G.; Loveridge, T.; Clough, J. M. J. Chem. Soc., Chem. Commun. 1995, 817.
23. (e) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, F.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 2135.
24. (f) Fretzen, A.; Kundig, E. P. Helv. Chim. Acta 1997, 80, 2023.
25. (g) Han, J. W.; Son, S. U.; Chung, Y. K. J. Org. Chem. 1997, 62, 8264.
26. For other examples using silyl migrations for tandem bond formations, see: (a) Matsuda, I.; Murata, S.; Ishii, Y. J. Chem. Soc., Perkin Trans. 1 1979, 26.
27. (b) Isobe, M.; Kitamura, M.; Goto, T. Tetrahedron Lett. 1979, 3465.
28. (c) Fleming, I.; Floyd, C. D. J. Chem. Soc., Perkin Trans. 1 1981, 969.
29. (d) Tietze, L. F.; Geissler, H.; Gewert, J. A.; Jakobi, U. Synlett 1994, 511.
30. (e) Shinokubo, H.; Miura, K.; Oshima, K.; Utimoto, K. Tetrahedron 1996, 52, 503.
31. (f) Smith, A. B., III.; Boldi, A. M. J. Am. Chem. Soc. 1997, 119, 6925.
32. (g) Takeda, K.; Nakajima, A.; Takeda, M.; Okamoto, Y.; Sato, T.; Yoshii, E.; Koizumi, T.; Shiro, M. J. Am. Chem. Soc. 1998, 120, 4947.
33. (h) Brauer, N.; Dreessen, S.; Schaumann, E. Tetrahedron Lett. 1999, 40, 2921.
34. Davies, S. G.; Goodfellow, C. L. J. Chem. Soc., Perkin Trans. 1 1990, 393.
35. All of the studies involve racemic arene complex 1. The relative stereochemistry of the major product diastereomers is illustrated, and is in agreement with the work of Davies.
36. 13C NMR, IR, and high-resolution mass spectroscopy.