Stereoselective preparation of 3-amino-2-fluoro carboxylic acid derivatives, and their incorporation in tetrahydropyrimidin-4(1H)-ones, and in open-chain and cyclic β-peptides

Helvetica Chimica Acta

Volumn 94, Issue 11, 2011, Pages 1908-1942

  Yoshinari, Tomohiro ^a   Gessier, François ^a   Noti, Christian ^a   Beck, Albert K ^a   Seebach, Dieter ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Amino acids; Cyclo peptides; Fluorine compounds; Peptides; Pyrimidinones, tetrahydro ; Stereoselective syntheses

Indexed keywords

AMINO ACID RESIDUES; BOND ANGLE; CARBOXYLIC ACID DERIVATIVES; CD SPECTRA; HEXAPEPTIDES; KARPLUS PARAMETERS; PYRIMIDINONES, TETRAHYDRO-; SIDE-CHAINS; STEREOSELECTIVE PREPARATION; STEREOSELECTIVE SYNTHESIS; STRUCTURAL DATA; TETRA PEPTIDE;

CARBOXYLIC ACIDS; FLUORINE; FLUORINE COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDES; STEREOCHEMISTRY; STEREOSELECTIVITY; SULFUR;

AMINO ACIDS;

1,2,3,4 TETRAHYDROPYRIMIDINE DERIVATIVE; 2,2 DIFLUORO 3 AMINO CARBOXYLIC ACID DERIVATIVE; ALANINE; BETA AMINO ACID; CARBOXYLIC ACID DERIVATIVE; CYCLOPEPTIDE; HEXAPEPTIDE; LEUCINE; PYRIMIDINONE DERIVATIVE; TETRAPEPTIDE; THREONINE; UNCLASSIFIED DRUG; VALINE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; FLUORINE NUCLEAR MAGNETIC RESONANCE; INFRARED SPECTROMETRY; MASS SPECTROMETRY; MELTING POINT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 81255165667     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.201100340     Document Type: Article

References (76)

1. R. I. Mathad, F. Gessier, D. Seebach, B. Jaun, Helv. Chim. Acta 2005, 88, 266.
2. G. Deniau, D. Seebach, Helv. Chim. Acta 2009, 92, 1720.
3. F. Gessier, C. Noti, M. Rueping, D. Seebach, Helv. Chim. Acta 2003, 86, 1852.
4. D. F. Hook, F. Gessier, C. Noti, P. Kast, D. Seebach, ChemBioChem 2004, 5, 691.
5. R. I. Mathad, B. Jaun, O. Flögel, J. Gardiner, M. Löweneck, J. D. C. Codée, P. H. Seeberger, D. Seebach, M. K. Edmonds, F. H. M. Graichen, A. D. Abell, Helv. Chim. Acta 2007, 90, 2251.
6. B. Jaun, D. Seebach, R. I. Mathad, Helv. Chim. Acta 2011, 94, 355.
7. L. Hunter, K. A. Jolliffe, M. J. T. Jordan, P. Jensen, R. B. Macquart, Chem.-Eur. J. 2011, 17, 2340.
8. Z. Gattin, W. F. van Gunsteren, J. Phys. Chem. B 2009, 113, 8695.
9. W. J. Middleton, J. Org. Chem. 1975, 40, 574
10. J. A. Wilkinson, Chem. Rev. 1992, 92, 505
11. R. P. Singh, J. M. Shreeve, Synthesis 2002, 2561.
12. E. Differding, H. Ofner, Synlett 1991, 187
13. G. S. Lal, G. P. Pez, R. G. Syvret, Chem. Rev. 1996, 96, 1737.
14. M. T. Reetz, M. W. Drewes, A. Schmitz, Angew. Chem. 1978, 99, 1186
15. Angew. Chem., Int. Ed. 1987, 26, 1141
16. M. T. Reetz, M. W. Drewes, R. Schwickardi, Org. Synth. 2004, Coll. Vol. 10, 256.
17. M. T. Reetz, M. W. Drewes, K. Harms, W. Reif, Tetrahedron Lett. 1988, 29, 3295
18. M. T. Reetz, Angew. Chem. 1991, 103, 1559
19. Angew. Chem., Int. Ed. 1991, 30, 1531
20. M. T. Reetz, Pure Appl. Chem. 1992, 64, 351
21. M. T. Reetz, Chem. Rev. 1999, 99, 1121.
22. M. A. Schwindt, D. T. Belmont, M. Carlson, L. C. Franklin, V. S. Hendrickson, G. L. Karrick, R. W. Poe, D. M. Sobieray, J. Van de Vusse, J. Org. Chem. 1996, 61, 9564.
23. M. Braun, A. Vonderhagen, D. Waldmüller, Liebigs Ann. Chem. 1995, 1447
24. S. Marcotte, X. Pannecouke, C. Feasson, J.-C. Quirion, J. Org. Chem. 1999, 64, 8461
25. M. J. Tozer, T. F. Herpin, Tetrahedron 1996, 52, 8619.
26. L. Somekh, A. Shanzer, J. Am. Chem. Soc. 1982, 104, 5836
27. D. Gani, P. B. Hitchcock, D. W. Young, J. Chem. Soc., Perkin Trans. 1 1985, 1363
28. P. E. Floreancig, S. E. Swalley, J. W. Trauger, P. B. Dervan, J. Am. Chem. Soc. 2000, 122, 6342.
29. P. C. Andrews, V. Bhaskar, K. M. Bromfield, A. M. Dodd, P. J. Duggan, S. A. M. Duggan, T. D. McCarthy, Synlett 2004, 791
30. V. Peddie, M. Pietsch, K. M. Bromfield, R. N. Pike, P. J. Duggan, A. D. Abell, Synthesis 2010, 1845.
31. D. Seebach, H. Estermann, Tetrahedron Lett. 1987, 28, 3103
32. H. Estermann, D. Seebach, Helv. Chim. Acta 1988, 71, 1824.
33. E. Juaristi, D. Quintana, B. Lamatsch, D. Seebach, J. Org. Chem. 1991, 56, 2553
34. D. Seebach, B. Lamatsch, R. Amstutz, A. K. Beck, M. Dobler, M. Egli, R. Fitzi, M. Gautschi, B. Herradón, P. C. Hidber, J. J. Irwin, R. Locher, M. Maestro, T. Maetzke, A. Mouriño, E. Pfammatter, D. A. Plattner, C. Schickli, W. B. Schweizer, P. Seiler, G. Stucky, W. Petter, J. Escalante, E. Juaristi, D. Quintana, C. Miravitlles, E. Molins, Helv. Chim. Acta 1992, 75, 913
35. E. Juaristi, J. Escalante, B. Lamatsch, D. Seebach, J. Org. Chem. 1992, 57, 2396
36. P. Murer, B. Rheiner, E. Juaristi, D. Seebach, Heterocycles 1994, 39, 319
37. E. Juaristi, D. Seebach, 'Enantioselective Synthesis of α-Substituted and α,β-Disubstituted β-Amino Acids via Chiral Derivatives of 3-Aminopropionic Acid', in 'Enantioselective Synthesis of β-Amino Acids', Ed. E. Juaristi, John Wiley & Sons, New York, 1997, Chapter 13, pp. 261-277
38. D. Seebach, A. Boog, W. B. Schweizer, Eur. J. Org. Chem. 1999, 335.
39. D. N. J. White, C. Morrow, P. J. Cox, C. N. C. Drey, J. Lowbridge, J. Chem. Soc., Perkin Trans. 2 1982, 239
40. J. Lowbridge, E. Mtetwa, R. J. Ridge, C. N. C. Drey, J. Chem. Soc., Perkin Trans. 1 1986, 155
41. D. Seebach, M. Overhand, F. N. M. Kühnle, B. Martinoni, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1996, 79, 913
42. J. L. Matthews, K. Gademann, B. Jaun, D. Seebach, J. Chem. Soc., Perkin Trans. 1 1998, 3331
43. K. Gademann, D. Seebach, Helv. Chim. Acta 1999, 82, 957
44. K. Gademann, D. Seebach, Helv. Chim. Acta 2001, 84, 2924
45. J. L. Matthews, M. Overhand, F. N. M. Kühnle, P. E. Ciceri, D. Seebach, Liebigs Ann. Recl. 1997, 1371
46. F. Büttner, M. Erdélyi, P. I. Arvidsson, Helv. Chim. Acta 2004, 87, 2735
47. F. Fujimura, M. Fukuda, J. Sugiyama, T. Morita, S. Kimura, Org. Biomol. Chem. 2006, 4, 1896
48. S. Fournel, S. Wieckowski, W. Sun, N. Trouche, H. Dumortier, A. Bianco, O. Chaloin, M. Habib, J.-C. Peter, P. Schneider, B. Vray, R. E. Toes, R. Offringa, C. J. M. Melief, J. Hoebeke, G. Guichard, Nat. Chem. Biol. 2005, 1, 377
49. M. Habib, M. N. Rivas, M. Chamekh, S. Wieckowski, W. Sun, A. Bianco, N. Trouche, O. Chaloin, H. Dumortier, M. Goldman, G. Guichard, S. Fournel, B. Vray, J. Immunol. 2007, 178, 6700.
50. K. Gademann, M. Ernst, D. Hoyer, D. Seebach, Angew. Chem. 1999, 111, 1302
51. Angew. Chem., Int. Ed. 1999, 38, 1223
52. K. Gademann, M. Ernst, D. Seebach, D. Hoyer, Helv. Chim. Acta 2000, 83, 16
53. P. W. Sutton, A. Bradley, J. Farràs, P. Romea, F. Urpì, J. Vilarrasa, Tetrahedron 2000, 56, 7947
54. D. Seebach, J. L. Matthews, A. Meden, T. Wessels, C. Baerlocher, L. B. McCusker, Helv. Chim. Acta 1997, 80, 173
55. H. C. Le, T. Hintermann, T. Wessels, Z. Gan, D. Seebach, R. R. Ernst, Helv. Chim. Acta 2001, 84, 208
56. T. D. Clark, L. K. Buehler, M. R. Ghadiri, J. Am. Chem. Soc. 1998, 120, 651
57. M. Royo, J. Farrera-Sinfreu, L. Solé, F. Albericio, Tetrahedron Lett. 2002, 43, 2029
58. F. Büttner, A. S. Norgren, S. Zhang, S. Prabpai, P. Kongsaeree, P. I. Arvidsson, Chem.-Eur. J. 2005, 11, 6145
59. D. Seebach, E. Dubost, R. I. Mathad, B. Jaun, M. Limbach, M. Löweneck, O. Flögel, J. Gardiner, S. Capone, A. K. Beck, H. Widmer, D. Langenegger, D. Monna, D. Hoyer, Helv. Chim. Acta 2008, 91, 1736.
60. N. Trouche, S. Wieckowski, W. Sun, O. Chaloin, J. Hoebeke, S. Fournel, G. Guichard, J. Am. Chem. Soc. 2007, 129, 13480.
61. M.-O. Ebert, B. Jaun, T. Yoshinari, W. B. Schweizer, L. McCusker, D. Sisak, D. Seebach, in preparation.
62. Prof. Dr. J. Escalante, personal communication
63. J. Escalante, P. Flores, J. M. Priego, Heterocycles 2004, 63, 2019
64. J. Escalante, C. Ortíz-Nava, P. Flores, J. M. Priego, C. García-Martínez, Molecules 2007, 12, 173.
65. U. Schmidt, H. Griesser, A. Lieberknecht, J. Talbiersky, Angew. Chem. 1981, 93, 271
66. Angew. Chem., Int. Ed. 1981, 20, 280
67. U. Schmidt, A. Lieberknecht, H. Griesser, J. Talbiersky, J. Org. Chem. 1982, 47, 3261
68. U. Schmidt, Nachr. Chem. Tech. Lab. 1981, 93, 271.
69. D. Seebach, A. K. Beck, D. J. Bierbaum, 'Die Welt der β- und Î-Peptide aus homologisierten proteinogenen Aminosäuren und anderen Bausteinen', VHCA, Zürich, 2004
70. D. Seebach, A. K. Beck, D. J. Bierbaum, Chem. Biodiversity 2004, 1, 1111.
71. D. Seebach, J. V. Schreiber, S. Abele, X. Daura, W. F. van Gunsteren, Helv. Chim. Acta 2000, 83, 34
72. D. Seebach, T. Sifferlen, P. A. Mathieu, A. M. Häne, C. M. Krell, D. J. Bierbaum, S. Abele, Helv. Chim. Acta 2000, 83, 2849
73. A. Glättli, X. Daura, D. Seebach, W. F. van Gunsteren, J. Am. Chem. Soc. 2002, 124, 12972
74. X. Daura, D. Bakowies, D. Seebach, J. Fleischhauer, W. F. van Gunsteren, P. Krüger, Eur. Biophys. J. 2003, 32, 661.
75. S.-S. Wang, B. F. Gisin, D. P. Winter, R. Makofske, I. D. Kulesha, C. Tzougraki, J. Meienhofer, J. Org. Chem. 1977, 42, 1286.
76. J. Podlech, D. Seebach, Liebigs Ann. Chem. 1995, 1217.