Selective esterifications of alcohols and phenols through carbodiimide couplings

Organic and Biomolecular Chemistry

Volumn 2, Issue 3, 2004, Pages 397-401

  Shelkov, Rimma ^a   Nahmany, Moshe ^a   Melman, Artem ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATION; ADDITION REACTIONS; ALCOHOLS; CATALYSIS; ESTERIFICATION; MOLECULAR STRUCTURE; PHENOLS; REACTION KINETICS; SUBSTITUTION REACTIONS;

ASYMMETRIC ANYDRIDES; CARBODIIMIDE COUPLINGS; CHEMOSELECTIVITY; HIGHLY ACIDIC PHENOLS; KETENE;

CARBOXYLIC ACIDS;

EID: 1342324606     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b312559a     Document Type: Article

References (52)

1. (a) A. Williams and I. T. Ibrahim, Chem. Rev, 1967, 67, 107 107
2. (b) D. Rich and J. Singh, in The Peptides, ed. E. Gross, vol. 1, Academic Press, New York., 1979, 241-261
3. (c) J. S. Albert and A. D. Hamilton, in Encyclopedia of Reagents for Organic Synthesis, ed. LO. A. Paquette, Wiley, Chichester, 1995, vol. 3, pp. 1751-1755.
4. (a) F. Albericio, R. Chinchilla, D. J. Dodsworth and C. Najera, Org. Prep. Proc. Int., 2001, 33, 203-305
5. (b) J. R. Spencer, V. V. Antonenko, N. G. J. Delaet and M. Goodman Int. J. Pept. Protein Res., 1992, 40, 282-293
6. (c) F. Albericio and L. A. Carpino, Methods Enzymol., 1997, 289, 104-126
7. (d) M. F. Songster and G. Barany Methods Enzymol., 1997, 289, 126-174
8. (e) H. T. Li, X. H. Jiang, Y. H. Ye, C. X. Fan, T. Romoff and M. Goodman, Org. Lett., 1999, 1, 91-93
9. (f) E. Falb, Y. Yechezkel, Y. Salitra and C. Gilon J. Pept. Res., 1999, 53, 507-517.
10. (a) M. Bodanszky, Peptide Chemistry: A Practical Textbook, Springer, New York, 1988
11. (b) S. S. Wang, J. P. Tam, B. S. Wang and R. B. Merrifield, Int. J. Pept. Protein Res., 1981, 19, 459.
12. (a) F. M. F. Chen, K. Kuroda and N. L. Bentoiton, Synthesis, 1978, 928-929
13. (b) D. H. Rammler and H. G. Khorana, J. Am. Chem. Soc., 1963, 85, 1997-2002.
14. B. Neises and W. Steglich, Org. Synth., 1985, 63, 183.
15. (a) J. R. Grunwell and D. L. Foerst Synth. Commun., 1976, 6, 453-455
16. (b) K. Horiki, Synth. Commun., 1977, 7, 251-259.
17. (a) A. Hassner and V. Alexanian, Tetrahedron Lett., 1978, 4457-4478
18. (b) K. Holmberg and B. Hansen, Acta Chem. Scand., 1979, 33, 410-412.
19. (a) D. J. Hudson, Org. Chem., 1988, 53, 617-624
20. (b) N. L. Benoiton and F. M. F. Chen, Can. J. Chem., 1981, 59, 384-389
21. (c) G. Barany and R. Merrifield, in The Peptides, Analysis, Synthesis, and Biology, eds. E. Gross and J. Meienhofer, Academic Press, New York, 1980, vol. 2A, pp. 123-127.
22. The rate of formation of symmetric anhydrides from O-acyl isoureas substatially slows down in polar solvents like DMF, see ref. 8a.
23. (a) M. Nahmany and A. Melman Org. Lett., 2001, 3, 3733-3735
24. (b) R. Shelkov, M. Nahmany and A. Melman J. Org. Chem., 2002, 67, 8975-8982.
25. 1H NMR analysis of the reaction mixture.
26. a values see: (a) CRC Handbook of Biochemistry and Molecular Biology, 3rd edn, CRC Press, Ohio, 1975-1976, 314-315
27. (b) Tables of Rate and Equilibrium Constants of Heterolytic Organic Reactions, ed. V. A. Palm., VINITI, Moscow, 1975, 32-96
28. (c) D. E. Ames and T. F. Grey, J. Chem. Soc., 1955, 631.
29. (a) H. Meyer, H. Wengenroth and W. Lauer, Chem. Ber., 1988, 121, 1643-1646
30. (b) A. D. Allen, M. A. McAllister and T. T. Tidwell, Tetrahedron Lett., 1993, 34, 1095-1098
31. (c) D. M. Birney and P. E. Wagenseller, J. Am. Chem. Soc., 1994, 116, 6262-6270
32. (d) W. W. Shumway, N. K. Dalley and D. M. Birney, J. Org. Chem., 2001, 66, 5832-5839
33. (e) For competitive trapping of trifluoroethanol by acylketene see: D. M. Birney, X. Xu, S. Ham and X. Huang, J. Org. Chem, 1997, 62, 7114-7120.
34. A very recent work provides an indirect way to obtain similar selectivity through the Mitsunobu reaction: (a) G. Appendino, A. Minassi, N. Daddario, F. Bianchi and G. Tron, Org. Lett., 2002, 4, 3839-3841
35. (b) For similar selectivity in Lewis catalyzed acylations see: K. L. Chandra, P. Saravan and V. K. Singh, Tetrahedron, 2002, 58, 1369-1374.
36. a of unsubstituted carbodiimide see: (a) S. V. Hill, A. Williams and J. L. Longridge J. Chem. Soc., Perkin Trans. 2, 1984, 1009-1013
37. (b) A. Williams and I. T. Ibrahim, J. Am. Chem. Soc., 1981, 103, 7090-7095.
38. For evidence of basic catalysis by carbodiimides see J. Izdebski, A. Orlowska, R. Anulewicz, E. Witkowska and D. Fiertek, Int. J. Pept. Protein Res., 1994, 43, 184-189.
39. For early reports on the mechanism of carbodiimide coupling see: (a) H. G. Khorana, Chem. Rev., 1953, 53, 145-166
40. (b) H. G. Khorana, Chem. Ind., 1955, 1087-1088
41. (c) I. T. Ibrahim and A. Williams, J. Chem. Soc., Chem. Commun., 1980, 25-26.
42. For the formation on anhydrides see: F. M. F. Chen, K. Kuroda and N. L. Benoiton, Synthesis, 1978, 928-929.
43. (a) B. Kundu, Tetrahedron Lett., 1992, 33, 3193-3196
44. (b) B. J. Johnson and P. M. Jacobs, J. Chem. Soc., Chem. Commun., 1968, 73-74.
45. (a) I. J. Galpin, P. M. Hardy, G. W. Kenner, R. McDermott, R. Ramage, J. H. Seely and R. G. Tyson, Tetrahedron, 1979, 35, 2577-2582
46. (b) J. Huang and J. Hall, J. Chem. Res. Synop., 1991, 292-293
47. B. Castro, G. Evin, C. Selve and R. Seyer, Synthesis, 1977, 413-413.
48. M. Bodanszky, in The Peptides, ed. E. Gross, Academic Press, New York, vol. 1, 1979, 105-196.
49. 35% For acylation of o-cresol.
50. A. Williams and I. T. Ibrahim, J. Am. Chem. Soc., 1981, 103, 7090-7095.
51. J. Rebek and D. Feitler, J. Am. Chem. Soc., 1974, 96, 1606-1607.
52. D. F. DeTar and R. Silverstein, J. Am. Chem. Soc., 1966, 88, 1013-1019.