Base catalyzed racemization of amino acid derivatives

Tetrahedron Asymmetry

Volumn 22, Issue 8, 2011, Pages 851-856

  D'Arrigo, Paola ^a   Arosio, Dario ^a   Cerioli, Lorenzo ^a   Moscatelli, Davide ^a   Servi, Stefano ^a   Viani, Fiorenza ^b   Tessaro, Davide ^a  

^a POLITECNICO DI MILANO   (Italy)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; THIOESTER;

ACIDITY; AMINO ACID ANALYSIS; ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; DENSITY FUNCTIONAL THEORY; ENTHALPY; PRIORITY JOURNAL; RACEMIZATION; THERMODYNAMICS;

EID: 79960036110     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2011.05.005     Document Type: Article

References (45)

1. I. Ali, V.K. Gupta, H.Y. Aboul-Enein, P. Singh, and B. Sharma Chirality 19 2007 453 463
2. E.J. Ebbers, G.J.A. Ariaans, J.P.M. Houbiers, A. Bruggink, and B. Zwanenburg Tetrahedron 53 1997 9417 9476
3. K. Faber Chem. Eur. J. 7 2001 5004 5010
4. D. Tessaro, G. Molla, L. Pollegioni, and S. Servi W. Fessner, T. Anthonsen, Modern Biocatalysis 2008 Wiley-VCH Weinheim 195 223
5. C.C. Gruber, I. Lavandera, K. Faber, and W. Kroutil Adv. Synth. Catal. 348 2006 1789 1805
6. S. Caddick, and K. Jenkins Chem. Soc. Rev. 25 1996 447 456
7. M.T. Gihani, and J.M. Williams Curr. Opin. Chem. Biol. 3 1999 11 15
8. F.F. Huerta, A.B.E. Minidis, and J.E. Bäckvall Chem. Soc. Rev. 30 2001 321 331
9. R. Noyori, M. Tokunaga, and M. Kitamura Bull. Chem. Soc. Jpn. 68 1995 36 55
10. H. Stecher, and K. Faber Synthesis 1997 1 16
11. R. Azerad, and D. Buisson Curr. Opin. Biotechnol. 11 2000 565 571
12. H. Pellissier Tetrahedron 59 2003 8291 8327
13. B.A. Persson, F.F. Huerta, and J.E. Bäckvall J. Org. Chem. 64 1999 5237 5240
14. G.G. Smith, A. Khatib, and G.S. Reddy J. Am. Chem. Soc. 105 1983 293 295
15. R.S. Ward Tetrahedron: Asymmetry 6 1995 1475 1490
16. D. Arosio, A. Caligiuri, P. D'Arrigo, G. Pedrocchi-Fantoni, C. Rossi, C. Saraceno, S. Servi, and D. Tessaro Adv. Synth. Catal. 349 2007 1345 1348
17. S. Servi, D. Tessaro, and G. Pedrocchi-Fantoni Coord. Chem. Rev. 252 2008 715 726
18. G.G. Smith, and G.V. Reddy J. Org. Chem. 54 1989 4529 4535
19. R.F. Cookson Chem. Rev. 74 1974 5 28
20. W.L. Jorgensen, and J.M. Briggs J. Am. Chem. Soc. 111 1989 4190 4197
21. R.G. Pearson, and R.L. Dillon J. Am. Chem. Soc. 75 1953 2439 2443
22. J.P. Richard, and T.L. Amyes Curr. Opin. Chem. Biol. 5 2001 626 633
23. G. Schürmann Quant. Struct.-Act. Relat. 15 1996 121 132
24. J.R. Keeffe, A.J. Kresge, and N.P. Schepp J. Am. Chem. Soc. 112 1990 4862 4868
25. Y. Chiang, A.J. Kresge, Y.S. Tang, and J. Wirz J. Am. Chem. Soc. 106 1984 460 462
26. T.L. Amyes, J.P. Richard, and M. Novak J. Am. Chem. Soc. 114 1992 8032 8041
27. D.S. Tan, M.M. Guenter, and D.G. Drueckhammer J. Am. Chem. Soc. 117 1995 9093 9094
28. P.-J. Um, and D.G. Drueckhammer J. Am. Chem. Soc. 120 1998 5605 5610
29. J.P. Guthrie J. Phys. Org. Chem. 11 1998 632 641
30. F. Ding, J.M. Smith, and H. Wang J. Org. Chem. 74 2009 2679 2691
31. R. Gilson, and M.C. Durrant Dalton Trans. 2009 10223 10230
32. N. Goudarzi, and M. Goodarzi Mol. Phys. 107 2009 1495 1503
33. F.G. Bordwell Acc. Chem. Res. 21 1988 456 463
34. J.M. Ho, and M.L. Coote J. Chem. Theor. Comput. 5 2009 295 306
35. J.P. Richard, G. Williams, and J. Gao J. Am. Chem. Soc. 121 1999 715 726
36. P. Hohenberg, and W. Kohn Phys. Rev. B 136 1964 864
37. W. Kohn, and L.J. Sham Phys. Rev. A 140 1965 1133
38. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
39. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785
40. B. Kovacević, and Z.B. Maksić Org. Lett. 3 2001 1523 1526
41. B.J. Smith, and L. Radom J. Am. Chem. Soc. 115 1993 4885 4888
42. I. Tunon, E. Silla, and J. Tomasi J. Phys. Chem. 96 1992 9043 9048
43. M.P. Coles, P.J. Aragón-Sáez, S.H. Oakley, P.B. Hitchcock, M.G. Davidson, Z.B. Maksić, R. Vianello, I. Leito, I. Kaljurand, and D.C. Apperley J. Am. Chem. Soc. 131 2009 16858 16868
44. C.Y. Peng, P.Y. Ayala, H.B. Schlegel, and M.J. Frisch J. Comput. Chem. 17 1996 49 56
45. 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.; 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.; 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.; C. Y. Peng; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A.; Gaussian: Pittsburgh, 1998.