N-alkyloxycarbonyl-3-aryloxaziridines: Their preparation, structure, and utilization as electrophilic amination reagents

Chemistry - A European Journal

Volumn 3, Issue 10, 1997, Pages 1691-1709

  Vidal, Joëlle ^a   Damestoy, Stéphanie ^a   Guy, Laure ^a   Hannachi, Jean Christophe ^a   Aubry, André ^b   Collet, André ^a  

^a UNIVERSITÉ DE LYON   (France)

^b UNIVERSITÉ DE LORRAINE   (France)

Author keywords

Aminations; Electrophilic substitutions; Hydrazines; Oxaziridines; Pseudopeptides

Indexed keywords

EID: 0030865569     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970031019     Document Type: Article

References (81)

1. S. Andreae, E. Schmitz, Synthesis 1991, 327-341, and references cited therein.
2. Recent reviews on electrophilic animation: J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig, Organic Synthesis Highlights, VCH, Weinheim, 1991, pp. 45-53; E. Erdik, M. Ay, Chem. Rev. 1989, 89, 1947-1980. See also: C. Greek, L. Bischoff, F. Ferreira, J.-P. Genêt, J. Org. Chem. 1995, 60, 7010-7012; A. Alberti, F. Cane, P. Dembech, D. Lazzari, A. Ricci, G. Seconi, J. Org. Chem. 1996, 61, 1677-1681.
3. Recent reviews on electrophilic animation: J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig, Organic Synthesis Highlights, VCH, Weinheim, 1991, pp. 45-53; E. Erdik, M. Ay, Chem. Rev. 1989, 89, 1947-1980. See also: C. Greek, L. Bischoff, F. Ferreira, J.-P. Genêt, J. Org. Chem. 1995, 60, 7010-7012; A. Alberti, F. Cane, P. Dembech, D. Lazzari, A. Ricci, G. Seconi, J. Org. Chem. 1996, 61, 1677-1681.
4. Recent reviews on electrophilic animation: J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig, Organic Synthesis Highlights, VCH, Weinheim, 1991, pp. 45-53; E. Erdik, M. Ay, Chem. Rev. 1989, 89, 1947-1980. See also: C. Greek, L. Bischoff, F. Ferreira, J.-P. Genêt, J. Org. Chem. 1995, 60, 7010-7012; A. Alberti, F. Cane, P. Dembech, D. Lazzari, A. Ricci, G. Seconi, J. Org. Chem. 1996, 61, 1677-1681.
5. Recent reviews on electrophilic animation: J. Mulzer, H.-J. Altenbach, M. Braun, K. Krohn, H.-U. Reissig, Organic Synthesis Highlights, VCH, Weinheim, 1991, pp. 45-53; E. Erdik, M. Ay, Chem. Rev. 1989, 89, 1947-1980. See also: C. Greek, L. Bischoff, F. Ferreira, J.-P. Genêt, J. Org. Chem. 1995, 60, 7010-7012; A. Alberti, F. Cane, P. Dembech, D. Lazzari, A. Ricci, G. Seconi, J. Org. Chem. 1996, 61, 1677-1681.
6. W. Büchner, R. Schliebs, G. Winter, K. H. Büchel, Industrial Inorganic Chemistry, VCH, Weinheim, 1989, pp. 45.
7. E. Schmitz, S. Andreae, S. Schramm, F. M. Albert, D. Lohmann, DDR Patent 240818, 1986; Chem. Abstr. 1987, 107, 198926g.
8. J. Viret, J. Gabard, A. Collet, Tetrahedron 1987, 43, 891-894; J. Viret, A. Collet, A. Lecoq, M. Marraud, A. Aubry, New J. Chem. 1989, 13, 849-852; A. Aubry, J.-P. Mangeot, D. Bayeul, J. Vidal, S. Stérin, A. Collet, A. Lecoq, M. Marraud, Biopolymers 1991, 31, 793-801; M. Marraud, V. Dupont, V. Grand, S. Zercout, A. Lecoq, G. Boussard, J. Vidal, A. Collet, A. Aubry, ibid. 1993, 33, 1135-1148; A. Amour, A. Collet, C. Dubar, M. Reboud, Int. J. Pept. Protein Res. 1994, 43, 297-304; S. Zercout, A. Aubry, J. Vidal, A. Vicherat, V. Dupont, A. Collet, M. Marraud, ibid. 1994, 44, 378-387; S. Chen, R. A. Chrusciel, H. Nakanishi, A. Raktabutr, M. E. Johnson, A. Sato, D. Weiner, J. Hoxie, H. U. Saragovi, M. J. Greene, M. Kahn, Proc. Natl. Acad. Sci. USA, 1992, 89, 5872-5876.
9. J. Viret, J. Gabard, A. Collet, Tetrahedron 1987, 43, 891-894; J. Viret, A. Collet, A. Lecoq, M. Marraud, A. Aubry, New J. Chem. 1989, 13, 849-852; A. Aubry, J.-P. Mangeot, D. Bayeul, J. Vidal, S. Stérin, A. Collet, A. Lecoq, M. Marraud, Biopolymers 1991, 31, 793-801; M. Marraud, V. Dupont, V. Grand, S. Zercout, A. Lecoq, G. Boussard, J. Vidal, A. Collet, A. Aubry, ibid. 1993, 33, 1135-1148; A. Amour, A. Collet, C. Dubar, M. Reboud, Int. J. Pept. Protein Res. 1994, 43, 297-304; S. Zercout, A. Aubry, J. Vidal, A. Vicherat, V. Dupont, A. Collet, M. Marraud, ibid. 1994, 44, 378-387; S. Chen, R. A. Chrusciel, H. Nakanishi, A. Raktabutr, M. E. Johnson, A. Sato, D. Weiner, J. Hoxie, H. U. Saragovi, M. J. Greene, M. Kahn, Proc. Natl. Acad. Sci. USA, 1992, 89, 5872-5876.
10. J. Viret, J. Gabard, A. Collet, Tetrahedron 1987, 43, 891-894; J. Viret, A. Collet, A. Lecoq, M. Marraud, A. Aubry, New J. Chem. 1989, 13, 849-852; A. Aubry, J.-P. Mangeot, D. Bayeul, J. Vidal, S. Stérin, A. Collet, A. Lecoq, M. Marraud, Biopolymers 1991, 31, 793-801; M. Marraud, V. Dupont, V. Grand, S. Zercout, A. Lecoq, G. Boussard, J. Vidal, A. Collet, A. Aubry, ibid. 1993, 33, 1135-1148; A. Amour, A. Collet, C. Dubar, M. Reboud, Int. J. Pept. Protein Res. 1994, 43, 297-304; S. Zercout, A. Aubry, J. Vidal, A. Vicherat, V. Dupont, A. Collet, M. Marraud, ibid. 1994, 44, 378-387; S. Chen, R. A. Chrusciel, H. Nakanishi, A. Raktabutr, M. E. Johnson, A. Sato, D. Weiner, J. Hoxie, H. U. Saragovi, M. J. Greene, M. Kahn, Proc. Natl. Acad. Sci. USA, 1992, 89, 5872-5876.
11. J. Viret, J. Gabard, A. Collet, Tetrahedron 1987, 43, 891-894; J. Viret, A. Collet, A. Lecoq, M. Marraud, A. Aubry, New J. Chem. 1989, 13, 849-852; A. Aubry, J.-P. Mangeot, D. Bayeul, J. Vidal, S. Stérin, A. Collet, A. Lecoq, M. Marraud, Biopolymers 1991, 31, 793-801; M. Marraud, V. Dupont, V. Grand, S. Zercout, A. Lecoq, G. Boussard, J. Vidal, A. Collet, A. Aubry, ibid. 1993, 33, 1135-1148; A. Amour, A. Collet, C. Dubar, M. Reboud, Int. J. Pept. Protein Res. 1994, 43, 297-304; S. Zercout, A. Aubry, J. Vidal, A. Vicherat, V. Dupont, A. Collet, M. Marraud, ibid. 1994, 44, 378-387; S. Chen, R. A. Chrusciel, H. Nakanishi, A. Raktabutr, M. E. Johnson, A. Sato, D. Weiner, J. Hoxie, H. U. Saragovi, M. J. Greene, M. Kahn, Proc. Natl. Acad. Sci. USA, 1992, 89, 5872-5876.
12. J. Viret, J. Gabard, A. Collet, Tetrahedron 1987, 43, 891-894; J. Viret, A. Collet, A. Lecoq, M. Marraud, A. Aubry, New J. Chem. 1989, 13, 849-852; A. Aubry, J.-P. Mangeot, D. Bayeul, J. Vidal, S. Stérin, A. Collet, A. Lecoq, M. Marraud, Biopolymers 1991, 31, 793-801; M. Marraud, V. Dupont, V. Grand, S. Zercout, A. Lecoq, G. Boussard, J. Vidal, A. Collet, A. Aubry, ibid. 1993, 33, 1135-1148; A. Amour, A. Collet, C. Dubar, M. Reboud, Int. J. Pept. Protein Res. 1994, 43, 297-304; S. Zercout, A. Aubry, J. Vidal, A. Vicherat, V. Dupont, A. Collet, M. Marraud, ibid. 1994, 44, 378-387; S. Chen, R. A. Chrusciel, H. Nakanishi, A. Raktabutr, M. E. Johnson, A. Sato, D. Weiner, J. Hoxie, H. U. Saragovi, M. J. Greene, M. Kahn, Proc. Natl. Acad. Sci. USA, 1992, 89, 5872-5876.
13. J. Viret, J. Gabard, A. Collet, Tetrahedron 1987, 43, 891-894; J. Viret, A. Collet, A. Lecoq, M. Marraud, A. Aubry, New J. Chem. 1989, 13, 849-852; A. Aubry, J.-P. Mangeot, D. Bayeul, J. Vidal, S. Stérin, A. Collet, A. Lecoq, M. Marraud, Biopolymers 1991, 31, 793-801; M. Marraud, V. Dupont, V. Grand, S. Zercout, A. Lecoq, G. Boussard, J. Vidal, A. Collet, A. Aubry, ibid. 1993, 33, 1135-1148; A. Amour, A. Collet, C. Dubar, M. Reboud, Int. J. Pept. Protein Res. 1994, 43, 297-304; S. Zercout, A. Aubry, J. Vidal, A. Vicherat, V. Dupont, A. Collet, M. Marraud, ibid. 1994, 44, 378-387; S. Chen, R. A. Chrusciel, H. Nakanishi, A. Raktabutr, M. E. Johnson, A. Sato, D. Weiner, J. Hoxie, H. U. Saragovi, M. J. Greene, M. Kahn, Proc. Natl. Acad. Sci. USA, 1992, 89, 5872-5876.
14. J. Viret, J. Gabard, A. Collet, Tetrahedron 1987, 43, 891-894; J. Viret, A. Collet, A. Lecoq, M. Marraud, A. Aubry, New J. Chem. 1989, 13, 849-852; A. Aubry, J.-P. Mangeot, D. Bayeul, J. Vidal, S. Stérin, A. Collet, A. Lecoq, M. Marraud, Biopolymers 1991, 31, 793-801; M. Marraud, V. Dupont, V. Grand, S. Zercout, A. Lecoq, G. Boussard, J. Vidal, A. Collet, A. Aubry, ibid. 1993, 33, 1135-1148; A. Amour, A. Collet, C. Dubar, M. Reboud, Int. J. Pept. Protein Res. 1994, 43, 297-304; S. Zercout, A. Aubry, J. Vidal, A. Vicherat, V. Dupont, A. Collet, M. Marraud, ibid. 1994, 44, 378-387; S. Chen, R. A. Chrusciel, H. Nakanishi, A. Raktabutr, M. E. Johnson, A. Sato, D. Weiner, J. Hoxie, H. U. Saragovi, M. J. Greene, M. Kahn, Proc. Natl. Acad. Sci. USA, 1992, 89, 5872-5876.
15. J. Vidal, J. Drouin, A. Collet, J. Chem. Soc. Chem. Commun. 1991, 435-437.
16. J. Vidal, L. Guy, S. Stérin, A. Collet, J. Org. Chem. 1993, 58, 4791-4793.
17. J. Vidal, S. Damestoy, A. Collet, Tetrahedron Lett. 1995, 36, 1439-1442.
18. R. Charnas, K. Gubernator, I. Heinze, C. Hubschwerlen (Hoffmann-La Roche), EP 508234, 1992; Chem. Abstr. 1993, 119, 117025d.
19. A. Aubry, J.-P. Mangeot, J. Vidal, A. Collet, S. Zerkout, M. Marraud, Int. J. Peptide Protein Res. 1994, 43, 305-311.
20. D. A. Niederer, J. T. Kapron, J. C. Vederas, Tetrahedron Lett. 1993, 34, 6859-6862.
21. C. Klinguer, O. Melnyk, E. Loing, H. Gras-Masse, Tetrahedron Lett. 1996, 40, 7259-7262.
22. F. A. Davis, A. C. Scheppard, Tetrahedron 1989, 45, 5703-5742; F. A. Davis, B. C. Chen, Chem. Rev. 1992, 92, 919-934.
23. F. A. Davis, A. C. Scheppard, Tetrahedron 1989, 45, 5703-5742; F. A. Davis, B. C. Chen, Chem. Rev. 1992, 92, 919-934.
24. W. B. Jennings, S. P. Watson, D. R. Boyd, Tetrahedron Lett. 1989, 30, 235-238.
25. V. A. Petrov, G. Resnati, Chem. Rev. 1996, 96, 1809-1823.
26. M. J. Haddadin, J. P. Freeman, in The Chemistry of Heterocyclic Compounds (Eds.: A. Weissberger, E. C. Taylor), Vol. 42, Small Ring Heterocycles, Part 3 (Ed.: A. Hassner), Wiley, 1985, p. 283-350.
27. R. Kupfer, S., Meier, E. U. Würthwein, Synthesis 1984, 688.
28. Y. Usuki, Y. Wang, J. Aubé, J. Org. Chem. 1995, 60, 8028-8035 and references cited therein.
29. N-acylimines are very sensitive to nucleophilic addition; for instance, see H. Ulrich, B. Tucker, A. A. R. Sayigh, J. Org. Chem. 1968, 33, 2887-2889.
30. D. L. Ball, J. O. Edwards, J. Am. Chem. Soc. 1956, 78, 1125-1129.
31. B. M. Trost, R. Braslau, J. Org. Chem. 1988, 53, 532-537.
32. P. Kocienski, Protecting groups, Thieme, Stuttgart, 1994. See also R. Geiger, W. König, in The Peptides: Analysis, Synthesis, Biology, Vol 3, Protection of Functional Groups in Peptide Synthesis (Eds.: E. Gross, J. Meienhofer), Academic Press, 1981, pp. 3-88.
33. P. Kocienski, Protecting groups, Thieme, Stuttgart, 1994. See also R. Geiger, W. König, in The Peptides: Analysis, Synthesis, Biology, Vol 3, Protection of Functional Groups in Peptide Synthesis (Eds.: E. Gross, J. Meienhofer), Academic Press, 1981, pp. 3-88.
34. 3SiI.
35. For another preparation of 12e see A. M. Kanazawa, J.-N. Denis, A. E. Greene, J. Org. Chem. 1994, 59, 1238-1240.
36. Y. Ogata, Y. Sawaki, J. Am. Chem. Soc. 1973, 95, 4687-4692.
37. 2). Crystallographic data (excluding structure factors) for this structure have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100235. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB21EZ, UK (Fax: Int. code +(1223)336-033; e-mail: deposit@chemcrys.cam.ac.uk).
38. D. Jerslev, Acta Crystallogr. 1967, 23, 645-649.
39. W. H. Chen, W. H. Watson, F. A. Davis, J. F. Lamendola, U. K. Nadir, Acta Crystallogr. B 1978, 34, 2861-2863.
40. S. D. Cook, T. A. Hamor, W. A. Jennings, A. A. Tebbutt, S. P. Watson, D. R. Boyd, J. Chem. Soc. Perkin Trans. 2 1991, 1281-1285.
41. A. G. Orpen, L. Brammer, F. H. Allen, O. Kennard, D. G. Watson, R. Taylor, in Structure correlation, Vol. 2 (Eds.: H.-B. Bürgi, J. D. Dunitz), VCH, Weinheim, 1994, see Appendix A.
42. W. B. Jennings, D. R. Boyd, in Cyclic Organonitrogen Stereodynamics (Eds.: J. B. Lambert, Y. Takeushi), VCH, Weinheim, 1992, pp. 105-158.
43. Y. Takeushi In Cyclic Organonitrogen Stereodynamics (Eds.: J. B. Lambert, Y. Takeushi), VCH, Weinheim, 1992, pp. 9-30.
44. Review on aminimides: W. J. McKillip, E. A. Sedor, B. M. Cullbertson, S. Wawzonek, Chem. Rev. 1973, 73, 255-281.
45. W. W. Zajac, Jr, T. R. Walters, M. G. Darcy, J. Org. Chem. 1988, 53, 5856-5860.
46. L. Guy, Thèse de Doctorat, École Normale Supérieure de Lyon, 1995.
47. A. Collet, J. Vidal, J.-C. Hannachi, L. Guy (CNRS), Brevet français 95/10685, 1995; PCT WO 97/09303, 1997.
48. R. W. Hay, L. J. Porter, J. Chem. Soc. B. 1967, 1261-1264.
49. J. Viret, A. Collet, New. J. Chem. 1988, 12, 253-256; see also H. Niedrich, G. Köller, J. Prakt. Chem. 1974, 316, 729-740.
50. J. Viret, A. Collet, New. J. Chem. 1988, 12, 253-256; see also H. Niedrich, G. Köller, J. Prakt. Chem. 1974, 316, 729-740.
51. M. E. Jung, M. A. Lyster, J. Chem. Soc. Chem. Commun. 1978, 315-316.
52. F. A. Davis, A. C. Sheppard, J. Org. Chem. 1987, 52, 955-957.
53. Review on sulfilimines: T. L. Gilchrist, C. Moody, Chem. Rev. 1977, 77, 409-435.
54. 3PO) and 19.92 (14).
55. 31P NMR (δ in the range -30 to -50) and characterized by X-ray crystallography: W. S. Sheldrick, D. Schomburg, A. Schmidpeter, T. von Criegern, Chem. Ber. 1980, 113, 55-69; T. Sasaki, S. Eguchi, T. Okano, J. Am. Chem. Soc. 1983, 105, 5912-5913.
56. 31P NMR (δ in the range -30 to -50) and characterized by X-ray crystallography: W. S. Sheldrick, D. Schomburg, A. Schmidpeter, T. von Criegern, Chem. Ber. 1980, 113, 55-69; T. Sasaki, S. Eguchi, T. Okano, J. Am. Chem. Soc. 1983, 105, 5912-5913.
57. -1).
58. F. A. Davis, J. M. Billmers, D. J. Gosciniak, J. C. Towson, J. Org. Chem. 1986, 51, 4240-4245.
59. R. D. Bach, G. J. Wolber, J. Am. Chem. Soc. 1984, 106, 1410-1415.
60. R. D. Bach, B. A. Coddens, J. J. W. McDouall, H. B. Schlegel, J. Org. Chem. 1990, 55, 3325-3330.
61. R. D. Bach, J. L. Andrés, F. A. Davis, J. Org. Chem. 1992, 57, 613-618.
62. Y. Hata, M. Watanabe, J. Am. Chem. Soc. 1979, 101, 6671-6676; Y. Hata, M. Watanabe, J. Org. Chem. 1981, 46, 610-614.
63. Y. Hata, M. Watanabe, J. Am. Chem. Soc. 1979, 101, 6671-6676; Y. Hata, M. Watanabe, J. Org. Chem. 1981, 46, 610-614.
64. S. V. Varlamov, G. V. Shustov, A. Yu. Shibaev, Yu. P. Puzanov, I. I. Chervin, R. G. Kostyanovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 882-890.
65. J. Vidal, C. Claessens, A. Collet, unpublished results; see ref. [6].
66. PC model 5.0 from Serena Software. We found that the use of a NO bond slightly longer than that of the X-ray structure (≈1.6 Å instead of 1.493 Å) gave results easier to interpret in terms of MO assignments. Ab initio geometry optimization of the parent ring affords a NO distance of 1.53 Å; see ref. [47].
67. The HOMO is in both cases a π orbital localized on the aromatic ring. The HOMO and LUMO energies (in eV) respectively are calculated as -10.01/ -0.52 for 2a and -10.43/ -2.29 for 50.
68. D. J. Hart, K. I. Kanai, D. G. Thomas, T. K. Yang, J. Org. Chem. 1983, 48, 289-294.
69. C. Betschart, B. Schmidt, D. Seebach, Helv. Chim. Acta 1988, 71, 1999-2021.
70. M. Bodanszky, A. Bodanszky, The Practice of Peptide Synthesis, Springer, New York, 1984, p. 242.
71. H. Fritz, C. D. Weis, J. Org. Chem. 1978, 43, 4900-4901.
72. L. F. Fieser, M. Fieser, Reagents for Organic Synthesis, Vol. 1, Wiley, New York, 1967, p. 135.
73. T. Tsuji, E. M. Kosower, J. Am. Chem. Soc. 1971, 93, 1992-1999.
74. E. Schmitz, R. Ohme, S. Schramm, Chem. Ber. 1967, 100, 2600-2603.
75. R. V. Hoffman, H. V. Kim, Tetrahedron Lett. 1990, 31, 2953-2956.
76. E. Decorte, V. Caplar, A. Sega, V. Sunjic, Acta Pharm. Jugoslav. 1980, 30, 183-187.
77. H. Niedrich, Chem. Ber 1967, 100, 3283-3288.
78. P. Quitt, J. Hellerbach, K. Vogler, Helv. Chim. Acta 1963, 46, 327-332.
79. C. H. Heathcock, C. T. Buse, W. A. Kleschick, M. C. Pirrung, J. E. Sohn, J. Lampe, J. Org. Chem. 1980, 45, 1066-1081.
80. P. Münster, W. Steglich, Synthesis 1987, 223-225.
81. M. N. Sheng, J. G. Zajacek, J. Org. Chem. 1968, 33, 588-590.