Rationalization of anomalous nonlinear effects in the alkylation of substituted benzaldehydes

Journal of the American Chemical Society

Volumn 124, Issue 46, 2002, Pages 13652-13653

  Buono, Frederic ^a   Walsh, Patrick J ^b   Blackmond, Donna G ^a  

^a UNIVERSITY OF HULL   (United Kingdom)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZALDEHYDE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; NONLINEAR SYSTEM; REACTION ANALYSIS;

ALKYLATION; BENZALDEHYDES; KINETICS; MODELS, CHEMICAL;

EID: 0037145992     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027406r     Document Type: Article

References (15)

1. (a) Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353.
2. (b) Guillaneux, D.; Zhao, S. H.; Samuel, O.; Rainford, D.; Kagan, H. B. J. Am. Chem. Soc. 1994, 116, 9430.
3. Recent reviews: (a) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. 1998, 37, 2922.
4. (b) Avalos, M.; Babiano, R.; Cintas, P.; Jimenez, J. L.; Palacios, J. C. Tetrahedron: Asymmetry 1997, 8, 2997.
5. (c) Blackmond, D. G. Acc. Chem. Res. 2000, 33, 402.
6. Oguni, N.; Matsuda, Y.; Kaneko, T. J. Am. Chem Soc. 1988, 110, 7877.
7. (a) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. 1991, 30, 49.
8. (b) Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327.
9. (c) Kitamura, M.; Suga, S.; Oka, H.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 9800.
10. (a) Nugent, W. A. Chem. Commun. 1999, 1369.
11. (b) Rosner, T., Sears, P. J., Nugent, W. A.; Blackmond, D. G. Org. Lett. 2000, 2, 2511.
12. Chen, Y. K.; Costa, A. M.; Walsh, P. J. J. Am. Chem. Soc. 2001, 123, 5378.
13. The product ee and reaction rates for the strong and weak binding limits in eqs 2-5 refer to the effect that strongly or weakly binding substrates have on the monomer-dimer distribution established in Scheme 1b in the absence of substrate.
14. (a) Rosner, T.; Le Bars, J.; Pfaltz, A.; Blackmond, D. G. J. Am. Chem. Soc. 2001, 123, 1848.
15. (b) Blackmond, D. G.; McMillan, C. R.; Ramdeheel, S.; Schorm, A.; Brown, J. M. J. Am. Chem. Soc. 2001, 123, 10103.