Catalytic chemical amide synthesis at room temperature: One more step toward peptide synthesis

Journal of Organic Chemistry

Volumn 80, Issue 9, 2015, Pages 4532-4544

  Mohy El Dine, Tharwat ^a   Erb, William ^a   Berhault, Yohann ^a   Rouden, Jacques ^a   Blanchet, Jérôme ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; AMINO ACIDS; CATALYSTS; PEPTIDES;

AMIDE BOND; BOC-PROTECTED AMINO ACIDS; BORONIC ACID; DIPEPTIDE SYNTHESIS; FUNCTIONALIZED; PEPTIDE SYNTHESIS; ROOM TEMPERATURE; STABLE CATALYSTS;

AMIDES;

AMIDE; AMINO ACID; AMINO ACID DERIVATIVE; AROMATIC CARBOXYLIC ACID; BORONIC ACID DERIVATIVE; DIPEPTIDE; HETEROCYCLIC AMINE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL BOND; DENSITY FUNCTIONAL THEORY; ENANTIOMERIC RATIO; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHODOLOGY; PEPTIDE SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIZATION; ROOM TEMPERATURE; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; TEMPERATURE;

AMIDES; CATALYSIS; DIPEPTIDES; MOLECULAR STRUCTURE; TEMPERATURE;

EID: 84928910875     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00378     Document Type: Article

References (67)

1. Schotten, C. Ber. Dtsch. Chem. Ges. 1884, 17, 2544-2547
2. Baumann, E. Ber. Dtsch. Chem. Ges. 1886, 19, 3218-3222
3. Valeur, E.; Bradley, M. Chem. Soc. Rev. 2009, 38, 606-631
4. Lanigan, R. M.; Sheppard, T. D. Eur. J. Org. Chem. 2013, 7453-7465
5. Lundberg, H.; Tinnis, F.; Selander, N.; Adolfsson, H. Chem. Soc. Rev. 2014, 43, 2714-2742
6. Charville, H.; Jackson, D.; Hodges, G.; Whiting, A. Chem. Commun. 2010, 46, 1813-1823
7. Pattabiraman, V. R.; Bode, J. W. Nature 2011, 480, 471-479
8. Falque, V.; Montalbetti, C. A. G. N. Tetrahedron 2005, 61, 10827-10852
9. Lenstra, D. C.; Rutjes, F. P. J. T.; Mecinović, J. Chem. Commun. 2014, 50, 5763-5766
10. Lundberg, H.; Tinnis, F.; Adolfsson, H. Synlett 2012, 23, 2201-2204
11. Lundberg, H.; Tinnis, F.; Adolfsson, H. Chem.-Eur. J. 2012, 18, 3822-3826
12. Allen, C. L.; Chhatwal, A. R.; Williams, J. M. J. Chem. Commun. 2012, 48, 666-668
13. Nomura, R.; Nakano, T.; Yamada, Y.; Matsuda, H. J. Org. Chem. 1991, 56, 4076-4078
14. Hosseini-Sarvari, M.; Sharghi, H. J. Org. Chem. 2006, 71, 6652-6654
15. Shekhar, A. C.; Kurnar, A. R.; Sathaiah, G.; Paul, V. L.; Sridhar, M.; Rao, P. S. Tetrahedron Lett. 2009, 50, 7099-7101
16. Kim, J. G.; Jang, D. O. Synlett 2010, 1231-1234
17. Ishihara, K.; Ohara, S.; Yamamoto, H. Org. Lett. 2005, 7, 5043-5046
18. Ishihara, K.; Kondo, S.; Yamamoto, H. Synlett 2001, 1371-1374
19. Yamashita, R.; Sakakura, A.; Ishihara, K. Org. Lett. 2013, 15, 3654-3657
20. Arnold, K.; Davies, B.; Giles, R. L.; Grosjean, C.; Smith, G. E.; Whiting, A. Adv. Synth. Catal. 2006, 348, 813-820
21. Arnold, K.; Davies, B.; Herault, D.; Whiting, A. Angew. Chem., Int. Ed. 2008, 47, 2673-2676
22. Al Zoubi, R. M.; Marion, O.; Hall, D. G. Angew. Chem., Int. Ed. 2008, 47, 2876-2879
23. Gernigon, N.; Al Zoubi, R. M.; Hall, D. G. J. Org. Chem. 2012, 77, 8386-8400
24. Pelter, A.; Levitt, T. E.; Nelson, P. Tetrahedron 1970, 26, 1539-1544
25. Ishihara, K.; Ohara, S.; Yamamoto, H. J. Org. Chem. 1996, 61, 4196-4197
26. Liu, S.; Yang, Y.; Liu, X.; Ferdousi, F. K.; Batsanov, A. S.; Whiting, A. Eur. J. Org. Chem. 2013, 5692-5700
27. Erb, W.; Albini, M.; Rouden, J.; Blanchet, J. J. Org. Chem. 2014, 79, 10568-10580
28. Erb, W.; Hellal, A.; Albini, M.; Rouden, J.; Blanchet, J. Chem.-Eur. J. 2014, 20, 6608-6612
29. Marcelli, T. Angew. Chem., Int. Ed. 2010, 49, 6840-6843
30. Charville, H.; Jackson, D. A.; Hodges, G.; Whiting, A.; Wilson, M. R. Eur. J. Org. Chem. 2011, 5981-5990
31. Schellenberger, V.; Jakubke, H.-D. Angew. Chem., Int. Ed. 1991, 30, 1437-1449
32. Lombard, C.; Saulnier, J.; Wallach, J. M. Protein Pept. Lett. 2005, 7, 621-629
33. Qin, Xu.; Khuong, A. C.; Yu, Z.; Du, W.; Decatur, J.; Gross, R. A. Chem. Commun. 2013, 49, 385-387
34. Schustera, M.; Aaviksaarb, A.; Jakubke, H.-D. Tetrahedron 1990, 46, 8093-8102
35. A comprehensive handbook: Karlheinz, D.; Gröger, H.; May, O. Enzyme Catalysis in Organic Synthesis; 2012; Vol. 1.
36. Ulijn, R. V.; Baragan, B.; Halling, P. J.; Flitsch, S. L. J. Am. Chem. Soc. 2002, 124, 10988-10989
37. Becht, J.-M.; Ngouela, S.; Wagner, A.; Mioskowski, C. Tetrahedron 2004, 60, 6853-6857
38. Tan, N.; Chen, Y.; Zhou, Y.; Au, C.-T.; Yin, S.-F. ChemPlusChem. 2013, 78, 1363-1369
39. Padwa, A.; Cochran, J. E.; Kappe, C. O. J. Org. Chem. 1996, 61, 3706-3714
40. Takeda, N.; Nakamura, T.; Imamura, A.; Unno, M. Heteroat. Chem. 2011, 22, 438-445
41. Vak, D.; Chun, C.; Lee, C. L.; Kim, J.-J.; Kim, D.-Yu. J. Mater. Chem. 2004, 14, 1342-1346
42. Canete, A. F.; Salas, C. O.; Zacconi, F. C. Molecules 2013, 18, 398-407
43. Mahendar, L.; Satyanarayana, G. J. Org. Chem. 2014, 79, 2059-2074
44. Demir, A. S.; Findik, H. Tetrahedron 2008, 64, 6196-6201
45. Filthaus, M.; Oppel, I. M.; Bettinger, H. F. Org. Biomol. Chem. 2008, 6, 1201-1207
46. Ghosh, T.; Hart, H. J. Org. Chem. 1989, 54, 5073-5085
47. Chen, Z.-W.; Jiang, H.-F.; Pan, X.-Y.; He, Z.-J. Tetrahedron 2011, 67, 5920-5927
48. Chan, W.-K.; Ho, C.-M.; Wong, M.-K.; Che, C.-M. J. Am. Chem. Soc. 2006, 128, 14796-14797
49. Chiou, W.-H.; Lin, G.-H.; Hsu, C.-C; Chaterpaul, S. J.; Ojima, I. Org. Lett. 2009, 11, 2659-2662
50. Maki, T.; Ishihara, K.; Yamamoto, H. Org. Lett. 2006, 8, 1431-1434
51. Eli, Lilly. Patent: US3063822, 1962.
52. Chem. Abstr. 1963, 58, 4984.
53. Arjona, O.; Csaky, A. G.; Murcia, M. C.; Plumet, J. Helv. Chim. Acta 2001, 84, 3667-3672
54. Hassan, Z.; Akacha, A. B.; Zantour, H. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 2241-2253
55. Nordstrom, L. U.; Vogt, H.; Madsen, R. J. Am. Chem. Soc. 2008, 130, 17672-17673
56. Stein, M.; Breit, B. Angew. Chem., Int. Ed. 2013, 52, 2231-2234
57. Pintori, D. G.; Greaney, M. F. Org. Lett. 2011, 13, 5713-5715
58. Mak, X.-Y.; Ciccolini, R. P.; Robinson, J. M.; Tester, J. W.; Danheiser, R. L. J. Org. Chem. 2009, 74, 9381-9387
59. Ghosh, S.; Bhaumik, A.; Mondal, J.; Mallik, A.; Sengupta, S.; Mukhopadhyay, C. Green Chem. 2012, 14, 3220-3229
60. Cadoni, R.; Porcheddu, A.; Giacomelli, G.; De Luca, L. Org. Lett. 2012, 14, 5014-5017
61. Zhang, W.; Ready, J. M. Angew. Chem., Int. Ed. 2014, 53, 8980-8984
62. Zhang, W.; Ready, J. M. Angew. Chem. 2014, 53-126, 9126-9130
63. Venkov, A. P.; Vodenicharov, D. M.; Ivanov, I. I. Synthesis 1991, 6, 476-478
64. Trieu, T. H.; Dong, J.; Zhang, Q.; Zheng, B.; Meng, T.-Z.; Lu, X.; Shi, X.-X. Eur. J. Org. Chem. 2013, 16, 3271-3277
65. Watson, A. J. A.; Wakeham, R. J.; Maxwell, A. C.; Williams, J. M. J. Tetrahedron 2014, 70, 3683-3690
66. Nielsen, De. U.; Neumann, K.; Taaning, R. H.; Lindhardt, A. T.; Modvig, A.; Skrydstrup, T. J. Org. Chem. 2012, 77, 6155-6165
67. Mamillapalli, N. C.; Sekar, G. Chem. Commun. 2014, 50, 7881-7884