Regioselective rhodium-catalyzed hydroformylation of 1,3-dienes to highly enantioenriched β,γ-unsaturated aldehyes with diazaphospholane ligands

Organic Letters

Volumn 13, Issue 1, 2011, Pages 164-167

  Watkins, Avery L ^a   Landis, Clark R ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78650871933     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102797t     Document Type: Article

References (31)

1. For a recent review on enantioselective hydroformylation see
2. Breit, B.; Seiche, W. Synthesis 2001, 1
3. See for example
4. Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033
5. Dieguez, M.; Pamies, O.; Ruiz, A.; Claver, C. New J. Chem. 2002, 26, 827
6. Cobley, C. J.; Klosin, J.; Qin, C.; Whiteker, G. T. Org. Lett. 2004, 6, 3277
7. Cobley, C. J.; Gardner, K.; Klosin, J.; Praquin, C.; Hill, C.; Whiteker, G. T.; Zanotti-Gerosa, A.; Petersen, J. L.; Abboud, K. A. J. Org. Chem. 2004, 69, 4031
8. Yan, Y. J.; Zhang, X. M. J. Am. Chem. Soc. 2006, 128, 7198
9. Clark, T. P.; Landis, C. R.; Freed, S. L.; Klosin, J.; Abboud, K. A. J. Am. Chem. Soc. 2005, 127, 5040
10. Klosin, J.; Landis, C. R. Acc. Chem. Res. 2007, 40, 1251
11. Thomas, P. J.; Axtell, A. T.; Klosin, J.; Peng, W.; Rand, C. L.; Clark, T. P.; Landis, C. R.; Abboud, K. A. Org. Lett. 2007, 9, 2665
12. Watkins, A. L.; Hashiguchi, B. G.; Landis, C. R. Org. Lett. 2008, 10, 4553
13. See for example (+)-Ambruticin: Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 1072
14. Amphidinolixe, X.; Furstner, A.; Kattnig, E.; Lepage, O. J. Am. Chem. Soc. 2006, 128, 9194
15. Discodermolide, L. E.; Poree, F.; Bourin, A.; Barbion, J.; Agouridas, E.; Lannou, M.; Commercon, A.; Betzer, J.; Pancrazi, A.; Ardisson, J. Chem.-Eur. J. 2008, 14, 11092
16. Smejkal, T.; Han, H.; Breit, B.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 10036
17. Horiuchi, T.; Ohta, T.; Nozaki, K.; Takaya, H. Chem. Commun. 1996, 155
18. Horiuchi, T.; Ohta, T.; Shirakawa, E.; Nozaki, K.; Takaya, H. Tetrahedron 1997, 53, 7795
19. Kim, H.; MacMillan, D. W. C. J. Am. Chem. Soc. 2008, 130, 398
20. Clement, W. H.; Orchin, M. Ind. Eng. Chem. Prod. Res. Dev. 1965, 4, 283
21. Fell, B.; Bahrmann, H. J. Mol. Catal. 1977, 2, 211
22. Bahrmann, H.; Fell, B. J. Mol. Catal. 1980, 8, 329
23. Botteghi, C.; Branca, M.; Saba, A. J. Organomet. Chem. 1980, 184, C17
24. van Leeuwen, P. W. N. M.; Roobeek, C. F. J. Mol. Catal. 1985, 31, 345
25. Chalchat, J. C.; Garry, R. P.; Lecomte, E.; Michet, A. Flavour Fragrance J. 1991, 6, 178
26. Bertozzi, S.; Campigli, N.; Vitulli, G.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1995, 487, 41
27. Barros, H. J. V.; Hanson, B. E.; dos Santos, E. N.; Gusevskaya, E. V. Appl. Catal., A 2004, 278, 57
28. Barros, H. J. V.; da Silva, J. G.; Guimaraes, C. C.; dos Santos, E. N.; Gusevskaya, E. V. Organometallics 2008, 27, 4523
29. Ligands 1 and 2 are commercially available from Sigma Aldrich.
30. Fürstner, A.; Nevado, C.; Waser, M.; Tremblay, M.; Chevrier, C.; Teply, F.; Aissa, C.; Moulin, E.; Müller, O. J. Am. Chem. Soc. 2007, 129, 9150
31. Trost, B. M.; Machacek, M. R.; Aponick, A. Acc. Chem. Res. 2006, 39, 747