Poor enantioselectivity of the direct aldol reaction catalyzed by (S,S)-proline dipeptide: A density functional study

International Journal of Quantum Chemistry

Volumn 108, Issue 1, 2008, Pages 66-74

  Fan, Jian Fen ^a   Wu, Li Fen ^a   Tao, Fu Ming ^b  

^a SOOCHOW UNIVERSITY   (China)

^b CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

(s,S) proline dipeptide; B3LYP 6 31G*; Direct aldol reaction; Enantioselectivity

Indexed keywords

CARBONYL CARBON; DIPEPTIDE; DIRECT ALDOL REACTION;

CARBON; CATALYST ACTIVITY; DENSITY FUNCTIONAL THEORY; ENANTIOSELECTIVITY; MATHEMATICAL MODELS; NITROBENZENE;

PEPTIDES;

EID: 36248990270     PISSN: 00207608     EISSN: 1097461X     Source Type: Journal    
DOI: 10.1002/qua.21374     Document Type: Article

References (27)

1. Nelson, S. G. Tetrahedron Asymmetry 1998, 9, 357.
2. Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J Am Chem Soc 1997, 119, 9319.
3. Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J Am Chem Soc 1997, 119, 10859.
4. Carreira, E. M.; Lee, W.; Singer, R. A. J Am Chem Soc 1995, 117, 3649.
5. Wong, C. H.; Whiteside, G. M. Enzymes in Synthetic Organic Chemistry. Pergamon: Oxford, 1994.
6. Wong, C. H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew Chem Int Ed Engl 1995, 34, 412.
7. Fessner, W. D. Curr Opin Chem Biol 1998, 2, 85.
8. List, B.; Lerner, R. A.; Barbas, C. F., III. J Am Chem Soc 2000, 122, 2395.
9. Notz, W.; List, B. J Am Chem Soc 2000, 122, 7386.
10. List, B.; Pojarliev, P.; Castello, C. Org Lett 2001, 3, 573.
11. Remondy, J. L. J Mol Catal B 1998, 5, 331.
12. Houk, K. N.; Bahmanyar, S. J Am Chem Soc 2000, 123, 11273.
13. Bahmanyar, S.; Houk, K. N.; Martin, J. H.; List, B. J Am Chem Soc 2003, 125, 2475.
14. Kofoeb, J.; Nielsen, J.; Reymond, J. L. Bioorg Med Chem Lett 2003, 13, 2445.
15. Ding, Y. P.; Shen, Z. X. Chinese Chemical Research 2006, 17, 9.
16. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E., Jr.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, (version A. 7). Gaussian Inc.: Pittsburgh PA, 1998.
17. Becke, A. D. J Chem Phys 1993, 98, 1372.
18. Becke, A. D. J Chem Phys 1993, 98, 5648.
19. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J Phy Chem 1994, 98, 11623.
20. Lee, C.; Yang, W.; Parr, R. G. Phys Rev B 1987, 37, 785.
21. Onsager, L. J Am Chem Soc 1936, 58, 1486.
22. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J Chem Phys 1985, 83, 735.
23. Fan, J. F.; Wu, L. F. Acta Chimica Sinica 2005, 63, 677.
24. Fan, J. F.; Wu, L. F. Chinese J Struct Chem 2006, 25, 433.
25. Curtin, D. Y. Rec Chem Prog 1954, 14, 111.
26. Hammett, L. P. Physical Origanic Chemistry. McGraw-Hill: New York, Chapter 5, 1970.
27. Krattiger, P.; Kovasy, R.; Revell, J. D.; Ivan, S.; Wennemers, H. Org Lett 2005, 7, 1101.