New low-temperature NMR studies establish the presence of a second equatorial-apical isomer of [(R, S)-binaphos](CO)2RhH

Organometallics

Volumn 29, Issue 15, 2010, Pages 3362-3367

  Castillo Molina, Dante A ^a   Casey, Charles P ^b   Müller, Imke ^c   Nozaki, Kyoko ^d   Jäkel, Christoph ^a,c  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

^c BASF SE   (Germany)

^d UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DIRECT OBSERVATION; ENANTIOSELECTIVE; LOW TEMPERATURES; NMR SPECTROSCOPY; NMR STUDIES; RHODIUM HYDRIDES; TEMPERATURE RANGE;

CHELATION; EQUILIBRIUM CONSTANTS; FUZZY CONTROL; HYDROFORMYLATION; PHOSPHORUS COMPOUNDS; RHODIUM;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 77955169235     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om100323q     Document Type: Article

References (40)

1. Powell, J. R.; Ambre, J. J.; Ruo, T. I. The Efficacy and Toxicity of Drug Stereoisomers. In Drug Stereochemistry; Wainer, I. W.; Drayer, D. E., Eds.; Marcel Dekker: New York, 1988; pp 245 -270.
2. Botteghi, C.; Paganelli, S.; Schionato, A.; Marchetti, M. Chirality 1991, 3, 355
3. Chaudhari, R. V. Curr. Opin. Drug Discovery Dev. 2008, 11, 820
4. Botteghi, C.; Consiglio, G.; Pino, P. Chimia 1972, 26, 141
5. For reviews in asymmetric hydroformylation, see: Gladiali, S.; Bayón, J. C.; Claver, C. Tetrahedron: Asymmetry 1995, 6, 1453
6. Agbossou, F.; Carpentier, J.-F.; Mortreux, A. Chem. Rev. 1995, 95, 2485
7. Breit, B.; Seiche, W. Synthesis 2001, 1
8. Breit, B. Acc. Chem. Res. 2003, 36, 264
9. Claver, C.; Diéguez, M.; Pàmies, O.; Castillón, S. Top. Organomet. Chem. 2006, 18, 35
10. Klosin, J.; Landis, C. R. Acc. Chem. Res. 2007, 40, 1251
11. Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033
12. Nozaki, K. Chem. Rec. 2005, 5, 376
13. Nozaki, K.; Sakai, N.; Nanno, T.; Higashijima, T.; Mano, S.; Horiuchi, T.; Takaya, H. J. Am. Chem. Soc. 1997, 119, 4413
14. Kless, A.; Holz, J.; Heller, D.; Kadyrov, R.; Selke, R.; Fischer, C.; Börner, A. Tetrahedron: Asymmetry 1996, 7, 33
15. Deerenberg, S.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Organometallics 2000, 19, 2065
16. Pàmies, O.; Net, G.; Ruiz, A.; Claver, C. Tetrahedron: Asymmetry 2001, 12, 3441
17. Arena, C. G.; Faraone, F.; Graiff, C.; Tiripicchio, A. Eur. J. Inorg. Chem. 2002, 711
18. Rubio, M.; Suárez, A.; Álvarez, E.; Bianchini, C.; Oberhauser, W.; Peruzzini, M.; Pizzano, A. Organometallics 2007, 26, 6428
19. Robert, T.; Abiri, Z.; Wassenaar, J.; Sandee, A. J.; Romanski, S.; Neudörfl, J.-M.; Schmalz, H.-G.; Reek, J. N. H. Organometallics 2010, 29, 478
20. Zhang, X.; Cao, B.; Yan, Y.; Yu, S.; Ji, B.; Zhang, X. Chem.-Eur. J. 2010, 16, 871
21. Casey, C. P.; Paulsen, E. L.; Beuttenmueller, E. W.; Proft, B. R.; Matter, B. A.; Powell, D. R. J. Am. Chem. Soc. 1999, 121, 63
22. Scheuermann née Taylor, C. J.; Jaekel, C. Adv. Synth. Catal. 2008, 350, 2708.
23. -1).
24. See Supporting Information.
25. Rossi, A. R.; Hoffmann, R. Inorg. Chem. 1975, 14, 365
26. Landis, C. R.; Firman, T. K.; Root, D. M.; Cleveland, T. J. Am. Chem. Soc. 1998, 120, 1842
27. Horiuchi, T.; Shirakawa, E.; Nozaki, K.; Takaya, H. Organometallics 1997, 16, 2981
28. Chan, A. S. C.; Pluth, J. J.; Halpern, J. J. Am. Chem. Soc. 1980, 102, 5952
29. Landis, C.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 1746
30. Feldgus, S.; Landis, C. R. J. Am. Chem. Soc. 2000, 122, 12714
31. Ahlrichs, R.; Bär, M.; Häser, M.; Horn, H.; Kölmel, C. Chem. Phys. Lett. 1989, 162, 165
32. Becke, A. D. Phys. Rev. A 1988, 38, 3098
33. Perdew, J. Phys. Rev. B 1986, 33, 8822 (erratum: 1986, 34, 7406).
34. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200
35. Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571
36. Eichkorn, K.; Treutler, O.; Öhm, H.; Häser, M.; Ahlrichs, R. Chem. Phys. Lett. 1995, 240, 283 (erratum: 1995, 242, 652).
37. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785
38. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
39. Vosko, S. H.; Wilk, L.; Nusair, M. Can J. Phys. 1980, 58, 1200
40. Schäfer, A.; Huber, C.; Ahlrichs, R. J. Chem. Phys. 1994, 100, 5829