New Applications of Camphor-Derived P,N-Ligands for Asymmetric Pd- and Ir-Catalyzed Reactions

Synlett

Volumn , Issue 14, 2003, Pages 2240-2242

  Bunlaksananusorn, Tanasri ^a   Luna, Alejandro Pérez ^b   Bonin, Martine ^b   Micouin, Laurent ^b   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

^b FACULTÉ DES SCIENCES PHARMACEUTIQUES ET BIOLOGIQUES   (France)

Author keywords

Asymmetric catalysis; Ir catalyzed hydroboration; meso bicyclic hydrazine; P,N ligands; T BuOk catalyzed addition

Indexed keywords

ALCOHOL; BICYCLO COMPOUND; CAMPHOR; HYDRAZINE DERIVATIVE; HYDROCARBON; IRIDIUM; LIGAND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; HYDROBORATION; OXIDATION; QUANTUM YIELD;

EID: 0242659866     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42067     Document Type: Article

References (31)

1. (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
2. (b) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: Weinheim, 2000, 1.
3. (c) Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pflatz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, 121.
4. (d) Togni, A.; Halterman, R. L. Metallocenes, Vol. 2; Wiley-VCH: Weinheim, 1998, 685.
5. (e) Beller, M.; Eckert, M. Angew. Chem. Int. Ed. 2000, 39, 1010; Angew. Chem. 2000, 112, 1027.
6. (e) Beller, M.; Eckert, M. Angew. Chem. Int. Ed. 2000, 39, 1010; Angew. Chem. 2000, 112, 1027.
7. Bunlaksanusorn, T.; Polborn, K.; Knochel, P. Angew. Chem. Int. Ed. 2003, 42, Angew. Chem. 3941; 2003, 115, 4071.
8. Bunlaksanusorn, T.; Polborn, K.; Knochel, P. Angew. Chem. Int. Ed. 2003, 42, Angew. Chem. 3941; 2003, 115, 4071.
9. (a) Pérez Luna, A.; Bonin, M.; Micouin, L.; Husson, H.-P. J. Am. Chem. Soc. 2002, 124, 12098.
10. (b) Pérez Luna, A.; Ceschi, M.-A.; Bonin, M.; Micouin, L.; Husson, H.-P.; Gougeon, S.; Estenne-Bouhtou, G.; Marabout, B.; Sevrin, M.; George, P. J. Org. Chem. 2002, 67, 3522.
11. (a) Helmchen, G.; Pfaltz, P. Acc. Chem. Res. 2000, 33, 336.
12. (b) Togni, A.; Bieler, N.; Burckhardt, C.; Köllner, C.; Pioda, G.; Schneider, R.; Schnyder, A. Pure Appl. Chem. 1999, 71, 1531.
13. (c) Loiseleur, O.; Hayashi, M.; Keenan, M.; Schmees, N.; Pflatz, A. J. Organomet. Chem. 1999, 576, 16.
14. (d) Roesky, P. W. Heteroatom Chem. 2002, 13, 514.
15. (e) Von Matt, P.; Loiseleur, O.; Koch, G.; Pfaltz, A.; Lefeber, C.; Feucht, T.; Helmchen, G. Tetrahedron: Asymmetry 1994, 5, 573.
16. (f) Dawson, G. J.; Williams, J. M. J.; Coote, S. J. Tetrahedron: Asymmetry 1995, 6, 2535.
17. (g) Hou, D.-R.; Reibenspies, J.; Colacot, T. J.; Burgess, K. Chem.-Eur. J. 2001, 7, 5391.
18. (h) Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem. 1998, 110, 3047; Angew. Chem. Int. Ed. 1998, 37, 2897.
19. (h) Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem. 1998, 110, 3047; Angew. Chem. Int. Ed. 1998, 37, 2897.
20. McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1983, 24, 979.
21. (a) Negishi, E.-I. Acc. Chem. Res. 1982, 15, 340.
22. (b) Negishi, E.-I. In Metal-Catalyzed Cross Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, Chap. 1.
23. (c) Erdik, E. Tetrahedron 1992, 48, 9577.
24. (a) Rodriguez, A. L.; Bunlaksananusorn, T.; Knochel, P. Org. Lett. 2000, 2, 3285.
25. (b) Bunlaksananusorn, T.; Rodriguez, A. L.; Knochel, P. Chem. Commun. 2001, 745.
26. (c) Bunlaksananusorn, T.; Knochel, P. Tetrahedron Lett. 2002, 43, 5817.
27. Uozumi, Y.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 9887.
28. Männig, D.; Nöth, H. Angew. Chem. Int. Ed. 1985, 24, 878; Angew. Chem. 1985, 97, 854.
29. Männig, D.; Nöth, H. Angew. Chem. Int. Ed. 1985, 24, 878; Angew. Chem. 1985, 97, 854.
30. Schnyder, A.; Togni, A.; Wiesli, U. Organometallics 1997, 16, 255.
31. r (min) = 14.6 (1S,4R,5R), 16.4 (1R,4S,5S)].