Asymmetric hydroformylation of vinylfurans catalyzed by {(11bS)-4-{[(1R)-2′-phosphino[1,1′-binaphthalen]-2-yl]oxy} dinaphtho[2,1-d:1′,2′-f]-[1,3,2]dioxaphosphepin}rhodium(I) [Rh I{(R,S)-binaphos}] derivatives

Helvetica Chimica Acta

Volumn 89, Issue 8, 2006, Pages 1681-1686

  Nakano, Koji ^a   Tanaka, Ryo ^a   Nozaki, Kyoko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ALDEHYDES; CATALYSIS; CATALYST SELECTIVITY; CATALYSTS; REACTION KINETICS;

ENANTIOMERIC PURITY; ENANTIOSELECTIVITIES; HYDROFORMYLATION; VINYLFURANS;

FURAN RESINS;

2 VINYLFURAN; 3 HYDROXY 2 METHYLPROPIONIC ACID; 3 VINYLFURAN; [4 [[2' PHOSPHINO (1,1' BINAPHTHALEN) 2 YL]OXY]DINAPHTHO[2,1 D:1',2' F][1,3,2]DIOXAPHOSPHEPIN]RHODIUM; ALCOHOL; ALDEHYDE DERIVATIVE; FURAN DERIVATIVE; RHODIUM COMPLEX; SODIUM BOROHYDRIDE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; DRUG STRUCTURE; ENANTIOMER; HYDROFORMYLATION; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 33748440642     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200690166     Document Type: Article

References (34)

1. K. Nozaki, I. Ojima, in 'Catalytic Asymmetric Synthesis', 2nd edn., Ed. I. Ojima, Wiley-VCH, New York, 2000, Chapt. 7.
2. K. Nozaki, in 'Comprehensive Asymmetric Catalysis', Eds. E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin, 1999, Vol. 1, Chapt. 11.
3. 'Rhodium Catalyzed Hydroformylation', Eds. P. W. N. M. van Leeuwen, C. Claver, Kluwer Academic Publishers, Dordrecht, 2000.
4. G. J. H. Buisman, L. A. vanderVeen, A. Klootwijk, W. G. J. deLange, P. C. J. Kamer, P. W. N. M. van Leeuwen, D. Vogt, Organometallics 1997, 16, 2929.
5. K. Nozaki, N. Sakai, T. Nanno, T. Higashijima, S. Mano, T. Horiuchi, H. Takaya, J. Am. Chem. Soc. 1997, 119, 4413.
6. T. Horiuchi, T. Ohta, E. Shirakawa, K. Nozaki, H. Takaya, Tetrahedron 1997, 53, 7795.
7. T. Horiuchi, T. Ohta, K. Nozaki, H. Takaya, Chem. Commun. 1996, 155.
8. T. Nanno, N. Sakai, K. Nozaki, K. Takaya, Tetrahedron: Asymmetry 1995, 6, 2583.
9. N. Sakai, S. Mano, K. Nozaki, H. Takaya, J. Am. Chem. Soc. 1993, 115, 7033.
10. T. Horiuchi, T. Ohta, E. Shirakawa, K. Nozaki, H. Takaya, J. Org. Chem. 1997, 62, 4285.
11. R. Lazzaroni, R. Settambolo, S. Rocchiccioli, S. Paganelli, M. Marchetti, J. Organomet. Chem. 2005, 690, 1699.
12. R. Lazzaroni, R. Settambolo, A. Caiazzo, M. A. Bennett, Organometallics 2002, 21, 2454.
13. A. Caiazzo, R. Settambolo, L. Pontorno, R. Lazzaroni, J. Organomet. Chem. 2000, 599, 298.
14. R. Settambolo, S. Scamuzzi, A. Caiazzo, R. Lazzaroni, Organometallics 1998, 17, 2127.
15. R. Settambolo, S. Pucci, S. Bertozzi, R. Lazzaroni, J. Organomet. Chem. 1995, 489, C50.
16. C. Basoli, C. Botteghi, M. A. Cabras, G. Chelucci, M. Marchetti, J. Organomet. Chem. 1995, 488, C20.
17. R. Lazzaroni, R. Settambolo, M. Mariani, A. Caiazzo, J. Organomet. Chem. 1999, 592, 69.
18. A. Caiazzo, R. Settambolo, G. Uccello-Barretta, R. Lazzaroni, J. Organomet. Chem. 1997, 548, 279.
19. R. Settambolo, A. Caiazzo, R. Lazzaroni, J. Organomet. Chem. 1996, 506, 337.
20. P. Kalck, F. Sereinspirau, New J. Chem. 1989, 13, 515.
21. A. F. Browning, A. D. Bacon, C. White, D. J. Milner, J. Mol. Catal. 1993, 83, L11.
22. G. Schmid, T. Fukuyama, K. Akasaka, Y. Kishi, J. Am. Chem. Soc. 1979, 101, 259.
23. J. Merten, R. Fröhlich, P. Metz, Angew. Chem., Int. Ed. 2004, 43, 5991.
24. A. Bierstedt, J. Stolting, R. Fröhlich, P. Metz, Tetrahedron: Asymmetry 2001, 12, 3399.
25. J. K. Stille, H. Su, P. Brechot, G. Parrinello, L. S. Hegedus, Organometallics 1991, 10, 1183.
26. K. Nozaki, T. Matsuo, F. Shibahara, T. Hiyama, Organometallics 2003, 22, 594.
27. K. Nozaki, T. Matsuo, F. Shibahara, T. Hiyama, Adv. Synth. Catal. 2001, 343, 61.
28. I. G. John, L. Radom, J. Am. Chem. Soc. 1978, 100, 3981.
29. W. H. Miles, E. J. Fialcowitz, E. S. Halstead, Tetrahedron 2001, 57, 9925.
30. N. Cohen, W. F. Eichel, R. J. Lopresti, C. Neukom, G. Saucy, J. Org. Chem. 1976, 41, 3505.
31. J. Retey, F. Lynen, Biochem. Z. 1965, 342, 256.
32. U. Schmidt, J. Werner, Synthesis 1986, 986.
33. U. Hersel, M. Steck, K. Seifert, Eur. J. Org. Chem. 2000, 1609.
34. U. Schmidt, J. Gombos, E. Haslinger, H. Zak, Chem. Ber. 1976, 109, 2628.