Synthesis of ω-(hetero)arylalkynylated α-amino acid by sonogashira-type reactions in aqueous media

Journal of Organic Chemistry

Volumn 71, Issue 20, 2006, Pages 7870-7873

  Brea, Roberto J ^a   López Deber, M Pilar ^a   Castedo, Luis ^a   Granja, Juan R ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ELECTRONS; HALOGEN COMPOUNDS; PALLADIUM COMPOUNDS; REACTION KINETICS;

CROSS-COUPLING REACTIONS; ELECTRON-POOR ARYL; PALLADIUM-CATALYSIS;

AMINO ACIDS;

ALKYNE DERIVATIVE; ALPHA AMINO ACID; AMINO ACID DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

AMINO ACID SYNTHESIS; AQUEOUS SOLUTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; SONOGASHIRA REACTION; STRUCTURE ANALYSIS;

ALKYNES; AMINO ACIDS, AROMATIC; CATALYSIS; GLYCINE; HYDROCARBONS, HALOGENATED; PALLADIUM; SOLUTIONS; WATER;

EID: 33749121805     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061300n     Document Type: Article

References (67)

1. For research on the design of peptide sequences with a predictable three-dimensional structure, see for example: (a) Struthers, M. D.; Cheng, R. P.; Imperiali, B. Science 1996, 271, 342-345.
2. (b) Zondlo, N. J.; Schepartz, A. J. Am. Chem. Soc. 1999, 121, 6938-6939.
3. (c) De Alba, E.; Santoro, J.; Rico, M.; Jiménez, M. A. Protein Sci. 1999, 8, 854-865.
4. (d) Baltzer, L.; Nilsson, H.; Nilsson, J. Chem. Rev. 2001, 101, 3153-3163.
5. (e) Pokala, N.; Handel, T. M. J. Struct. Biol. 2001, 134, 269-281.
6. (f) Yadav, M. K.; Redman, J. E.; Leman, L. J.; Álvarez- Gutiérrez, J. M.; Zhang, Y.; Scout, C. D.; Ghadiri, M. R. Biochemistry 2005, 44, 9723-9732.
7. (a) Handel, T. M.; Williams, S. A.; DeGrado, W. F. Science 1993, 259, 1288-1293.
8. (b) Ghadiri, M. R.; Case, M. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1594-1597.
9. (c) Barthe, P.; Rochette, S.; Vita, C.; Roumestand, C. Protein Sci. 2000, 9, 942-955.
10. (d) Neidigh, J. W.; Fesinmeyer, R. M.; Andersen, N. H. Nat. Struct. Biol. 2002, 9, 425-430.
11. (e) Kelso, M. J.; Beyer, R. L.; Hoang, H. N.; Lakdawala, A. S.; Snyder, J. P.; Oliver, W. V.; Robertson, T. A.; Appleton, T. G.; Fairlie, D. P. J. Am. Chem. Soc. 2004, 126, 4828-4842.
12. (a) Imperiali, B.; Prins, T. J.; Fisher, S. L. J. Org. Chem. 1993, 58, 1613-1616.
13. (b) Rajashankar, K. R.; Ramakumar, S.; Jain, R. M.; Chauhan, V. S. J. Am. Chem. Soc. 1995, 117, 10129-10130.
14. (c) Nowick, J. S.; Chung, D. M.; Maitra, K.; Maitra, S.; Stigers, K. D.; Sun, Y. J. Am. Chem. Soc. 2000, 122, 7654-7661.
15. (d) Bilgiçer, B.; Kumar. K. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 15324-15329.
16. (a) Bark, S. J.; Kent, S. B. H. FEBS Lett. 1999, 460, 67-76.
17. (b) Duhamel, J.; Kanagalingam, S.; O'Brien, T. J.; Ingratta, M. W. J. Am. Chem. Soc. 2003, 125, 12810-12822.
18. (c) Gochin, M.; Guy, R. K.; Case, M. A. Angew. Chem., Int. Ed. 2003, 42, 5325-5328.
19. (d) Enander, K.; Dolphin, G. T.; Baltzer, L. J. Am. Chem. Soc. 2004, 126, 4464-4465.
20. (a) Roberts, D. C.; Vellaccio, F. In The Peptides; Gross, E., Meienhofer, J., Eds.; Academic Press: New York, 1983; Chapter 6.
21. (b) Fauchére, J.-L.; Thurieau, C. Adv. Drug Res. 1992, 23, 127-159.
22. Barrett, G. C.; Elmore, D. T. Amino Acids and Peptides; University Press: Cambridge, U.K., 1998.
23. Esposito, A.; Piras, P. P.; Ramazzotti, D.; Taddei, M. Org. Lett. 2001, 3, 3273-3275.
24. (a) Seayad, J.; List, B. Org. Biomol. Chem. 2005, 3, 719-724.
25. (b) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138-5175.
26. (a) Belokon, Y. N.; Bespalova, N. B.; Churkina, T. D.; Císarova, I.; Ezernitskaya, M. G.; Haratyunyan, S. R.; Hrdina, R.; Kagan, H. B.; Kocovsky, P.; Kochetkov, K. A.; Larionov, O. V.; Lyssenko, K. A.; North, M.; Polásek, M.; Peregudov, A. S.; Prisyazhnyuk, V. V.; Vyskocil, S. J. Am. Chem. Soc. 2003, 125 12860-12871.
27. (b) Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645-732.
28. (c) Ryan, S. J.; Zhang, Y.; Kennan, A. J. Org. Lett. 2005, 7, 4765-4767.
29. Barrett, G. C.; Davies, J. S. In Amino Acids, Peptides, and Proteins; The Royal Society of Chemistry: Cambridge, U.K., 2003; Vol. 34.
30. Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 2.
31. (a) Miyaura, N. Top. Curr. Chem. 2002, 219, 11-59.
32. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168.
33. (c) Collier, P. N.; Campell, A. D.; Patel, I.; Raynham, T. M.; Taylor, R. J. K. J. Org. Chem. 2002, 67, 1802-1815.
34. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 50, 4467-4470.
35. (b) Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313-3315.
36. (c) For a recent review, see: Sonogashira. K. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience; New York, 2002; pp 493-529.
37. (d) Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979-2017.
38. (e) Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566-1568.
39. (a) For a copper-free Sonogashira coupling, see: Soheili, A.; Albaneze-Walker, J.; Murry, J. A.; Dormer, P. G.; Hughes, D. L. Org. Lett. 2003, 5, 4191-4194.
40. (b) For Sonogashira cross-coupling of unactivated alkyl halides using carbene ligands, see: Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642-13643.
41. López-Deber, M. P.; Castedo, L.; Granja, J. R. Org. Lett. 2001, 3, 2823-2826.
42. (a) De la Rosa, M. A.; Velarde, E.; Guzmán, A. Synth. Commun. 1990, 20, 2059-2064.
43. (b) Marck, G.; Villiger, A.; Buchecker, R. Tetrahedron Lett. 1994, 35, 3277-3280.
44. (c) Bleicher, L. S.; Cosford, N.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109-1118.
45. (d) LeBlond, C. R.; Andrews, A. T.; Sun, Y.; Sowa, J. R., Jr. Org. Lett. 2001, 3, 1555-1557.
46. (e) For Sonogashira cross-coupling reactions using water-soluble catalysts, see: Dibowski, H.; Schmidtchen, F. P. Angew. Chem., Int. Ed. 1998, 37, 476-478.
47. Anderson, K. W.; Buchwald, S. L. Angew. Chem., Int. Ed. 2005, 44, 6173-6177.
48. Wolf, C.; Lerebours, R. Org. Biomol. Chem. 2004, 2, 2161-2164.
49. (f) For an example using diaryliodonium salts, see: Radhakrishnan, U.; Stang, P. J. Org. Lett. 2001, 3, 859-860.
50. (g) For an example of a copper-free coupling reaction in water see: Liang, B.; Dai, M.; Chen, J.; Yang, Z. J. Org. Chem. 2005, 70, 391-393.
51. Gala, D.; Stamford, A.; Jenkins, J.; Kugelman, M. Org. Process Res. Dev. 1997, 1, 163-164.
52. (a) Organic Reactions in Aqueous Media; Li, C.-J., Chan, T.-H., Eds.; Wiley: New York, 1997.
53. (b) Organic Synthesis in Water; Grieco, P. A., Ed.: Academic Press: Dordrecht, The Netherlands, 1997.
54. (c) Aqueous-Phase Organometallic Catalysis, 2nd ed.; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
55. (d) Shaughnessy, K. H.; DeVasher, R. B. Curr. Org. Chem. 2005, 9, 585-609.
56. N-modified amino acids are known to influence polypeptides containing them by (a) adopting an extended conformation and ensuring the adoption of a similar conformation by their N-terminal neighbours, see Stewart, D. E.; Sarkar, A.; Wampler, J. E. J. Mol. Biol. 1990, 214, 253-260;
57. (b) promoting the formation of β-turns, see Braun, W.; Kallen, J.; Mikol, V.; Walkinshaw, M. D.; Wuthrich, K. FASEB J. 1995, 9, 63-72;
58. Fusetani, N.; Matsunaga, S. Chem. Rev. 1993, 93, 1793-1806;
59. or (c) promoting the formation of left-handed α-helical structures, see Manavalan, P.; Momany, F. A. Biopolymers 1980, 19, 1943-1973.
60. (a) Van Hest, J. C. M.; Kiick, K. L.; Tirrell, D. A. J. Am. Chem. Soc. 1989, 122, 1282-1288.
61. (b) Baldwin, J. E.; Bradley, M.; Abbott, S. D.; Adlington, R. M. Tetrahedron 1991, 47, 5309-5328.
62. (c) Leukart, O.; Caviezel, M.; Eberle, A.; Escher, E.; Tun-Kyi, A.; Schwyzer, R. Helv. Chim. Acta 1976, 59, 2181-2183.
63. (d) Coulter, A. W.; Talalay, P. J. Biol. Chem. 1968, 243, 3238-3247.
64. (a) Chenault, H. K.; Dahmer, J.; Whitesides, G. M. J. Am. Chem. Soc. 1989, 111, 6354-6364.
65. (b) Wolf, L. B.; Tjen, K. C. M. F.; Rutjes, F. P. J. T.; Hiemstra, H.; Schoemaker, H. E. Tetrahedron Lett. 1998, 39, 5081-5084.
66. (a) On the importance of the solvent for the catalytic efficiency of Pd/C, see: Felpin, F.-X.; Vo-Thanh, G.; Villiéras, J.; Lebreton, J. Tetrahedron: Asymmetry 2001, 12, 1121-1124.
67. (b) Recently it has been shown that DMA-water solvent system reaction rates are comparable to the analogous homogeneous reactions, see: Novák, Z.; Szabó, A.; Répási, J.; Kotschy, A. J. Org. Chem. 2003, 68, 3327-3329.