Chiral olefins as steering ligands: Syntheses of C1-symmetric dibenzo[a,e]cyclooctenes (Rdbcot)

Organometallics

Volumn 24, Issue 12, 2005, Pages 2997-3007

  Läng, Florian ^a   Breher, Frank ^a   Stein, Daniel ^a   Grützmacher, Hansjörg ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; HYDROGENATION; IRIDIUM; ORGANOMETALLICS; RHODIUM; X RAY DIFFRACTION ANALYSIS;

ARYL ALKYL KETONES; BOAT CONFORMATION; STEERING LIGANDS; TRANSFERHYDROGENATION;

OLEFINS;

EID: 21244445784     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om050093z     Document Type: Article

References (46)

1. Rhodium cod complexes: Sharp, P. R. Comprehensive Organometallic Chemistry, 2nd ed.; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 8, pp 245-268.
2. (b) Iridium cod complexes: Sharp, P. R. Comprehensive Organometallic Chemistry, 2nd ed.; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds., Pergamon: Oxford, U.K., 1995; Vol. 8, pp 365-270.
3. Bernard, M.; Guiral, V.; Delbecq, F.; Fache, F.; Sautet, P.; Lemaire, M. J. Am. Chem. Soc. 1998, 120, 1441, and literature cited therein.
4. Petra, D. G. I.; Kamer, P. C. J.; Spek, A. L.; Schoemaker, H. E.; van Leeuwen, P. W. N. M. J. Org. Chem. 2000, 65, 3010.
5. Dahlenburg, L.; Götz, R. Eur. J. Inorg. Chem. 2004, 888.
6. (b) Dahlenburg, L.; Götz, R. J. Organomet. Chem. 2001, 619, 88.
7. For a short review see: Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 3364.
8. (a) Shintani, R.; Okamoto, K.; Otomaru, Y.; Ueyama, K.; Hayashi, T. J. Am. Chem. Soc. 2005, 127, 54.
9. (b) Tokunaga, N.; Otomaru, Y.; Okamoto, K.; Ueyama, K.; Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2004, 126, 13584.
10. (c) Hayashi, T.; Ueyama, K.; Tokunaga, N.; Yoshida, K. J. Am. Chem. Soc. 2003, 125, 11508.
11. (a) Defieber, C.; Paquin, J.-F.; Serna, S.; Carreira, E. M. Org. Lett. 2004, 6, 3873.
12. (b) Fischer, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1628.
13. (a) Grützmacher, H.; Deblon, S.; Maire, P.; Schönberg, H. Ger. Offen. DE 101 59 015.6, 2002.
14. (b) Maire, P.; Deblon, S.; Breher, F.; Geier, J.; Böhler, C.; Rüegger, H.; Grützmacher, H. Chem. Eur. J. 2004, 10, 4198,
15. Thomaier, J.; Boulmaâz, S.; Schönberg, H.; Rüegger, H.; Currao, A.; Grützmacher, H.; Hillebrecht, H.; Pritzkow, H. New J. Chem. 1998, 21, 947 and literature cited therein.
16. Fieser, L. F.; Pechet, M. J. Am. Chem. Soc. 1946, 68, 2577.
17. Irngartinger, H.; Reibel, W. R. K. Acta Crystallogr. 1981, B37, 1724.
18. Avram, M.; Dinu, D.; Mateescu, G.; Nenitzescu, C. D. Chem. Ber. 1960, 93, 1793.
19. Müller, J.; Göser, P.; Elian, M. Angew. Chem., Int. Ed. Engl. 1969, 8, 374.
20. Brown, M.; Zubkowski, J. D.; Valente, E. J.; Yang, G.; Henry, W. P. J. Organomet. Chem. 2000, 613, 111.
21. Douglas, A. R.; Crabtree, R. H. Organometallics 1983, 2, 621.
22. Anton, D. R.; Crabtree, R. H. Organometallics 1983, 2, 855.
23. Mak, T. C. W.; Wong, H. N. C.; Sze, K. H.; Book, L. J. Organomet. Chem. 1983, 255, 123.
24. Läng, F. ETH Dissertation No. 15845, 2004.
25. Chaffins, S.; Brettreich, M.; Wudl, F. Synthesis 2002, 1191.
26. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392.
27. 13C NMR Data for Organometallic Compounds; Academic Press: London, 1981; p 16.
28. Pimblett, G.; Garner, C. D.; Clegg, W. J. Chem. Soc., Dalton Trans. 1985, 1977.
29. -1, and the resolution of the enantiomers of mono-substituted cod derivatives could not be achieved: (a) Anet, F. A. L.; Bourn, A. J. R.; Lin, Y. S. J. Am. Chem. Soc. 1964, 86, 3576.
30. (b) Cope, A. C.; Meili, J. E. J. Am. Chem. Soc. 1967, 89, 1883. Also, the inversion barrier of other chiral dibenzo[o,e]cyclooctenes (dbcot's) with substituants attached to one of the benzo groups is too low to allow isolation in nonracemic form:
31. -1, which is sufficient to allow their isolation in enantiomerically pure form:
32. (d) Mislow, K.; Perlmutter, H. D. J. Am. Chem. Soc. 1962, 84, 3591.
33. (e) Salisbury, L. E. J. Org. Chem. 1978, 43, 26.
34. Albinati, A.; Arz, C.; Pregosin, P. S. Inorg. Chem. 1987, 26, 508.
35. Albinati, A.; Pregosin, P. S.; Wombacher, F. Inorg. Chem. 1989, 29, 1812.
36. Selected examples: (a) Tappe, K.; Knochel, P. Tetrahedron: Asymmetry 2004, 15, 91 and literature cited therein.
37. (b) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889, and literature cited therein.
38. (c) Burk, M. J.; Gross, M. F. Tetrahedron Lett. 1994, 35, 9363.
39. Gamez, P.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705.
40. Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579.
41. Schultz, A. G.; Harrington, R. E. J. Am, Chem. Soc. 1991, 113, 4926.
42. Evans, D. A.; Fu, G. C.; Hoveyda, A. H. J. Am. Chem. Soc. 1992, 114, 6671.
43. Pioda, G.; Togni, A. Tetrahedron: Asymmetry 1998, 9, 3903.
44. Dimitrov, V.; Kostova, K.; Genov, M. Tetrahedron Lett. 1996, 37, 6787.
45. Cahn, R. S.; Ingold, C. K.; Prelog, V. Angew. Chem. 1966, 78, 413.
46. Hayashi, T.; Ueyama, K.; Tokunaga, N.; Yoshida, K. J. Am. Chem. Soc. 2003, 125, 11508.