Theoretical study of the catalysis of cyanohydrin formation by the cyclic dipeptide catalyst cyc/o[(S)-his-(S)-Phe]

Journal of Organic Chemistry

Volumn 74, Issue 4, 2009, Pages 1464-1472

  Schoenebeck, Franziska ^a   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC ALDEHYDES; AROMATIC UNITS; AUTOINDUCTION; CATALYTIC SPECIES; CYCLIC DIPEPTIDE; DENSITY FUNCTIONAL; DIPEPTIDE; ENANTIOSELECTIVE; HIGH ENANTIOSELECTIVITIES; HYDROCYANATION; HYDROGEN BONDINGS; HYDROXY GROUPS; IMIDAZOLE GROUPS; MOLECULAR DYNAMICS METHODS; NON-POLAR; REACTION CONDITIONS; SUBSTRATE BINDINGS; THEORETICAL STUDIES; TRANSITION STATE;

ALDEHYDES; AROMATIC COMPOUNDS; CATALYSIS; DYNAMICS; ENANTIOSELECTIVITY; HYDROGEN; MOLECULAR DYNAMICS; MOLECULAR MECHANICS; REACTION KINETICS; STEREOCHEMISTRY;

DENSITY FUNCTIONAL THEORY;

ALDEHYDE; CYANOHYDRIN; DIMER; DIPEPTIDE; IMIDAZOLE; IMINE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ENANTIOSELECTIVITY; ENERGY; GAS; HYDROGEN BOND; ISOMERIZATION; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PEPTIDE ANALYSIS; PHYSICAL PHASE; STEREOCHEMISTRY;

ALDEHYDES; BIOCATALYSIS; DIPEPTIDES; ELECTRONS; MODELS, MOLECULAR; NITRILES; PEPTIDES, CYCLIC; QUANTUM THEORY; STATIC ELECTRICITY; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 64349102770     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801958r     Document Type: Article

References (44)

1. Inoue, S.; Oku, J.-I. J. Chem. Soc., Chem. Commun. 1981, 229.
2. (a) See also: North, M. Tetrahedron: Asymmetry 2003, 14, 147-176.
3. (b) For an early example of hydrocyanation, see: Lapworth, A. J. Chem. Soc. 1903, 83, 995-1005.
4. Becker, W.; Pfeil, E. J. Am. Chem. Soc. 1966, 88, 4299-4300.
5. Effenberger, F.; Stelzer, U. Angew. Chem., Int. Ed. 1991, 30, 873, and references therein.
6. (a) Tanaka, K.; Mori, A.; Inoue, S. J. Org. Chem. 1990, 55, 181.
7. (b) Matthews, B. R.; Jackson, W. R.; Jayatilake, G. S.; Wilshire, C.; Jacobs, H. Aust. J. Chem. 1988, 41, 1997.
8. Danda, H. Synlett 1991, 263-264.
9. Danda, H.; Nishikawa, H.; Otaka, K. J. Org. Chem. 1991, 56, 6740-6741.
10. Shvo, Y.; Gal, M.; Becker, Y.; Elgavi, A. Tetrahedron: Asymmetry 1996, 7, 911-924.
11. Kogut, E. F.; Thoen, J. C.; Lipton, M. A. J. Org. Chem. 1998, 63, 4604.
12. Jackson, W. R.; Jayatilake, G. S.; Matthews, B. R.; Wilshire, C. Aust. J. Chem. 1988, 41, 203-213.
13. Hogg, D. J. P.; North, M.; Stokoe, R. B. Tetrahedron: Asymmetry 1996, 7, 911-924.
14. For further studies that are consistent with the proposed mechanism, see: Prelog, V.; Wilhelm, M. Helv. Chim. Acta 1954, 37, 1634-1660.
15. For a study of further derivatives and a transition state proposal, see: Xie, L.; Hua, W.; Chan, A. S. C.; Leung, Y.-C. Tetrahedron: Asymmetry 1999, 10, 4715-4728.
16. Mori, A.; Ikeda, Y.; Kinoshita, K.; Inoue, S. Chem. Lett. 1989, 2119-2122.
17. North, M. Tetrahedron 1992, 48, 5509-5522.
18. Apperley, D.; North, M.; Stokoe, R. B. Tetrahedron: Asymmetry 1995, 6, 1869-1872.
19. Callant, D.; Coussens, B.; v. d. Maten, T.; de Vries, N. K. Tetrahedron: Asymmetry 1992, 2, 401-414.
20. Recent reviews: (a) Colby Davie, E. A.; Mennen, S. M.; Xu, Y.; Miller, S. J. Chem. Rev. 2007, 107, 5759-5812.
21. (b) Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520-1543.
22. Frisch, M. J. et al. Gaussian03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004. See Supporting Information for full reference.
23. Kaminski, G. A.; Friesner, R. A.; Tirado-Rives, J.; Jorgensen, W. L. J. Phys. Chem. B 2001, 105, 6474-6487.
24. MacroModel 5.1.016; Schrodinger, Inc.: Portland, OR, 2001. All rights reserved. RV7200801.
25. Li, J.; Jiang, W.-Y.; Han, K.-L.; He, G.-Z.; Li, C. J. Org. Chem. 2003, 68, 8786-8789.
26. Arnaud, R.; Adamo, C.; Cossi, M.; Milet, A.; Vallee, Y.; Barone, V. J. Am. Chem. Soc. 2000, 122, 324-330.
27. Kumeda, Y.; Minami, Y.; Takano, K.; Taketsugu, T.; Hirano, T. J. Mol. Structure (Theochem) 1999, 458, 285.
28. For the corresponding enzyme (oxynitrilase) mechanism, it was found that the addition step of the nucleophile on the aldehyde carbonyl is the rate-determining step (see: Ching, W.-M.; Kallen, R. G. J. Am. Chem. Soc. 1978, 100, 6119-6124). This seems to be the case in the catalysis by dipeptide 1 also, since electron-poor aldehydes are reported to react in shorter reaction times than their electron-rich counterparts (compare Figure 13).
29. The N⋯N-H distance of 2.99 A between the imidazole groups was frozen.
30. (a) Kaminski, G.; Jorgensen, W. L. J. Phys. Chem. 1996, 100, 18010-18013.
31. (b) Price, M. L. P.; Ostrovsky, D.; Jorgensen, W. L. J. Comput. Chem. 2001, 22, 1340-1352.
32. (c) Kaminski, G.; Friesner, R. A.; Tirado-Rives, J.; Jorgensen, W. L. J. Phys. Chem. B 2001, 105, 6474-6487.
33. By "catalytic distance" we mean the distances highlighted with dotted lines in the transition states in Figure 9 and Figure 10 (excluding jr-interac-tion).
34. Grimme, S. J. Comput. Chem. 2004, 25, 1463-1473.
35. (30) Grimme, S. Chem. Eur. J. 2004, 10, 3423-3429.
36. (a) Oku, J.; Ito, N.; Inoue, S. Makromol. Chem. 1982, 183, 579.
37. (b) Asada, S.; Kobayashi, Y.; Inoue, S. Makromol. Chem. 1985, 186, 1755.
38. For example: (a) Sculimbrene, B. R.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 10125-10126.
39. (b) Fierman, M. B.; O'Leary, D. J.; Steinmetz, W. E.; Miller, S. J. J. Am. Chem. Soc. 2004, 126, 6967-6971.
40. (c) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134-2136.
41. (d) Vasbinder, M. M.; Jarvo, E. R.; Miller, S. J. Angew. Chem., Int. Ed. 2001, 40, 2824-2827.
42. For example: (a) Zuend, S. J.; Jacobsen, E. N. J. Am. Chem. Soc. 2007, 129, 15872-15883.
43. (b) Huang, H.; Jacobsen, E. N. J. Am. Chem. Soc. 2006, 128, 7170-7171.
44. (c) Lalonde, M. P.; Chen, Y.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 6366-6370.