Screening of a modular sugar-based phosphite ligand library in the asymmetric nickel-catalyzed trialkylaluminum addition to aldehydes

Journal of Organic Chemistry

Volumn 71, Issue 21, 2006, Pages 8159-8165

  Mata, Yvette ^a   Diéguez, Montserrat ^a   Pàmies, Oscar ^a   Woodward, Simon ^b  

^a UNIVERSITAT ROVIRA I VIRGILI   (Spain)

^b UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

LIGANDS; PHOSPHITE MOIETIES; TRIALKYLALUMINUM;

ADDITION REACTIONS; ALDEHYDES; ALUMINUM COMPOUNDS; CATALYSIS; SUBSTITUTION REACTIONS; SUGARS;

PHOSPHORUS COMPOUNDS;

1,2:5,6 DI O ISOPROPYLIDENE 3 O [(3,3':5,5' TETRA TERT BUTYL 1,1' BIPHENYL 2,2' DIYL)PHOSPHITE] ALPHA DEXTRO GLUCOFURANOSE; ALDEHYDE; ALUMINUM DERIVATIVE; CARBOHYDRATE DERIVATIVE; FURAN DERIVATIVE; LIGAND; NICKEL; PHOSPHITE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 33750026134     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0613535     Document Type: Article

References (26)

1. Pu, L.; Yu, H. B. Chem. Rev. 2001, 101, 757.
2. Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry, 5th ed.; Wiley: New York, 1988; p 224.
3. (a) Chan, A. S. C.; Zhang, F.-Y.; Yip, C.-W. J. Am. Chem. Soc. 1997, 119, 4080.
4. (b) Pagenkopf, B. L.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 9593.
5. (c) Lu, J.-F.; You, J.-S.; Gau, H.-M. Tetrahedron: Asymmetry 2000, 11, 2531.
6. (d) You, J.-S.; Hsieh, S.-H.; Gau, H.-M. Chem. Commun. 2001, 1546.
7. (e) Biswas, K.; Prieto, O.; Goldsmith, P. J.; Woodward, S. Angew. Chem., Int. Ed. 2005, 44, 2232.
8. 3 to an aldehyde normally require catalyst loadings of 10-20%, see refs 3a-d.
9. See, for instance: (a) Diéguez, M.; Pàmies, O.; Claver, C. Chem. Rev. 2004, 104, 3189.
10. (b) Diéguez, M.; Pàmies, O.; Ruiz, A.; Díaz, Y.; Castillón, S.; Claver, C. Coord. Chem. Rev. 2004, 248, 2165.
11. (c) Diéguez, M.; Ruiz, A.; Claver, C. Dalton Trans. 2003, 2957.
12. (d) Pàmies, O.; Diéguez, M.; Ruiz, A.; Claver, C. Chem. Today 2004, 12.
13. (e) Diéguez, M.; Pàmies, O.; Ruiz, A.; Claver, C. In Methodologies in Asymmetric Catalysis; Malhotra, S. V., Ed.; American Chemical Society: Washington, DC, 2004.
14. (f) Diéguez, M.; Pàmies, O.; Claver, C. Tetrahedron: Asymmetry 2004, 15, 2113.
15. See, for instance: (a) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889.
16. (b) Reet, M. T.; Goossen, L. J.; Meiswinkel, A.; Paetzold, J.; Jense, J. F. Org. Lett. 2003, 5, 3099.
17. (c) Huang, H.; Zheng, Z.; Luo, H.; Bai, C.; Hu, X.; Chen, H. Org. Lett. 2003, 5, 4137.
18. (d) Huang, H.; Liu, X.; Chen, S.; Chen, H.; Zheng, Z. Tetrahedron: Asymmetry 2004, 15, 2011.
19. (e) Huang, H.; Liu, X.; Chen, H.; Zheng, Z. Tetrahedron: Asymmetry 2005, 16, 693.
20. Ligands 1a,c,e,f, 2e,f, and 4e,f have been previously synthesized, see: (a) Suarez, A.; Pizzano, A.; Fernández, I.; Khiar, N. Tetrahedron: Asymmetry 2001, 12, 633 and refs 6b,c.
21. Kartha, K. P. R. Tetrahedron Lett. 1986, 27, 3415.
22. Hollenberg, D. H.; Klein, R. S.; Fox, J. J. Carbohydr. Res. 1978, 67, 491.
23. Wang, H.; Ning, J. J. Org. Chem. 2003, 68, 2521.
24. Tu, Y.; Frohn, M.; Wang, Z.-X.; Shi, Y. In Organic Synthesis; Wolf, S., Ed.; 2003; p 1.
25. Beksan, E.; Schieberle, P.; Robert, F.; Blank, I.; Fay, L. B.; Schlichtherle-Cerny, H.; Hofmann, T. J. Agric. Food Chem. 2003, 51, 5428.
26. At high ligand-to-nickel ratio the disproportionation of benzaldehyde to benzoic acid and benzyl alcohol takes place.