Origins of the Stereodivergent Outcome in the Staudinger Reaction between Acyl Chlorides and Imines

Journal of Organic Chemistry

Volumn 63, Issue 17, 1998, Pages 5869-5876

  Arrieta, Ana ^a   Lecea, Begoña ^a   Cossío, Fernando P ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000344501     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9804745     Document Type: Article

References (76)

1. Staudinger, H. Justus Liebigs Ann. Chem. 1907, 356, 51.
2. (a) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5748.
3. (b) Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; pp 331-359.
4. (c) Tidwell, T. T. Ketenes; Wiley: New York, 1995; pp 518-527.
5. (a) Sheehan, J. C.; Ryan, J. J. J. Am. Chem. Soc. 1951, 73, 1204.
6. (b) Sheehan, J. C.; Corey, E. J. Org. React. 1958, 9, 388.
7. For a recent survey on activating reagents in the Staudinger reaction, see: Reference 2b, pp 299-330 and references therein.
8. (a) Ghosez, L.; Marchand-Brynaert, J. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 85.
9. (b) Thomas, R. C. In Recent Progress in the Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer: Berlin, 1988; p 533.
10. (c) van der Steen, F. H.; van Koten, G. Tetrahedron 1991, 47, 7503.
11. (d) Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982; Vols. 1-3.
12. (a) Manhas, M. S.; Amin, S. G.; Bose, A. K. Heterocycles 1976, 5, 699.
13. (b) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755.
14. (c) Ojima, I. Acc. Chem. Res. 1995, 28, 383.
15. (a) Molteni, V.; Annunziata, R.; Cinquini, M.; Cozzi, F.; Benaglia, M. Tetrahedron Lett. 1998, 39, 1257.
16. (b) Ruhland, B.; Bhandari, A.; Gordon, E. M.; Gallop, M. A. J. Am. Chem. Soc. 1996, 118, 253.
17. (a) Bose, A. K.; Anjaneyulu, B.; Bhattacharaya, S. K.; Manhas, M. S. Tetrahedron 1967, 23, 4769.
18. (b) Wells, J. N.; Lee, R. E. J. Org. Chem. 1969, 34, 1477.
19. (c) Nelson, D. A. J. Org. Chem. 1972, 37, 1447.
20. (d) Arrieta, A.; Lecea, B.; Palomo, C. J. Chem. Soc., Perkin Trans. 1 1987, 845.
21. (e) Bose, A. K.; Chang, Y. H.; Manhas, M. S. Tetrahedron Lett. 1972, 4091.
22. (f) Oshiro, Y.; Komatsu, M.; Vesaka, M.; Agawa, T. Heterocycles 1984, 22, 549.
23. (g) Doyle, T. W.; Belleau, B.; Luh, B.-Y.; Ferrari, C. F.; Cunningham, M. P. Can. J. Chem. 1977, 55, 468.
24. (h) Nelson, D. A. J. Org. Chem. 1972, 37, 1447.
25. Barbara, G.; Bataglia, A.; Bruno, C.; Giorgianni, P.; Guerrini, A. J. Org. Chem. 1996, 61, 8480.
26. Lynch, J. E.; Riseman, S. M.; Laswell, W. L.; Tschaen, D. M.; Volante, R. P.; Smith, G. B.; Shinkay, I. J. Org. Chem. 1989, 54, 3792.
27. Pacansky, J.; Chang, J. S.; Brown, D. W.; Schwarz, W. J. Org. Chem. 1982, 47, 2233.
28. (a) Cossío, F. P.; Ugalde, J. M.; Lopez, X.; Lecea, B.; Palomo, C. J. Am. Chem. Soc. 1993, 115, 995.
29. (b) Cossío, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085.
30. (c) Arrieta, A.; Ugalde, J. M.; Cossío, F. P.; Lecea, B. Tetrahedron Lett. 1994, 35, 4465.
31. (d) Arrastia, I.; Arrieta, A.; Ugalde, J. M.; Cossío, F. P.; Lecea, B. Tetrahedron Lett. 1994, 35, 7825.
32. (e) Lecea, B.; Arrastia, I.; Arrieta, A.; Roa, G.; Lopez, X.; Arriortua, M. I.; Ugalde, J. M.; Cossío, F. P. J. Org. Chem. 1996, 61, 3070.
33. Lopez, R.; Sordo, T. L.; Sordo, J. A.; González, J. J. Org. Chem. 1993, 58, 7036.
34. (a) Niwayama, S.; Kallel, E. A.; Spellmeyer, D. C.; Sheu, C.; Houk, K. N. J. Org. Chem. 1996, 61, 2813.
35. (b) Dolbier, W. R., Jr.; Korionak, H.; Houk, K. N.; Sheu, C. Acc. Chem. Res. 1996, 29, 471 and previous references therein.
36. Bose, A. K.; Spiegelman, G.; Manhas, M. S. Tetrahedron Lett. 1971, 3167.
37. (a) Duran, F.; Ghosez, L. Tetrahedron Lett. 1970, 245.
38. (b) Moore, H. W.; Hernández, L.; Chambers, R. J. Am. Chem. Soc. 1978, 100, 2245.
39. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 735.
40. GAUSSIAN 94, Revision B.2: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robbb, M. A.; Cheeseman, J. R.; Keith, T.; Peterson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 1995.
41. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986; pp 65-68 and references therein.
42. (a) Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford: New York, 1989.
43. (b) Bartolotti, L. J.; Fluchick, K. In Reviews in Computational Chemistry, Lipkowitz, K. B., Boyd, D. B., Eds.; VCH Publishers: New York, 1996; Vol. 7, pp 187-216.
44. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
45. (b) Becke, A. D. Phys. Rev. A 1998, 38, 3098.
46. (c) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1980, 37, 785.
47. (d) Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200.
48. See, for example: (a) Morao, I.; Lecea, B.; Cossío, F. P. J. Org. Chem. 1997, 62, 7033. (b) Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036. (c) Wiest, O.; Houk, K. N.; Black, K. A.; Thomas, B., IV. J. Am. Chem. Soc. 1995, 117, 8594. (d) Wiest, O.; Black, K. A.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 10336.
49. See, for example: (a) Morao, I.; Lecea, B.; Cossío, F. P. J. Org. Chem. 1997, 62, 7033. (b) Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036. (c) Wiest, O.; Houk, K. N.; Black, K. A.; Thomas, B., IV. J. Am. Chem. Soc. 1995, 117, 8594. (d) Wiest, O.; Black, K. A.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 10336.
50. See, for example: (a) Morao, I.; Lecea, B.; Cossío, F. P. J. Org. Chem. 1997, 62, 7033. (b) Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036. (c) Wiest, O.; Houk, K. N.; Black, K. A.; Thomas, B., IV. J. Am. Chem. Soc. 1995, 117, 8594. (d) Wiest, O.; Black, K. A.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 10336.
51. See, for example: (a) Morao, I.; Lecea, B.; Cossío, F. P. J. Org. Chem. 1997, 62, 7033. (b) Goldstein, E.; Beno, B.; Houk, K. N. J. Am. Chem. Soc. 1996, 118, 6036. (c) Wiest, O.; Houk, K. N.; Black, K. A.; Thomas, B., IV. J. Am. Chem. Soc. 1995, 117, 8594. (d) Wiest, O.; Black, K. A.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 10336.
52. McIver, J. W.; Komornicki, A. J. Am. Chem. Soc. 1972, 94, 2625.
53. Wiberg, K. B. Tetrahedron 1968, 24, 1083.
54. Wiberg, K. B.; Rabien, P. R. J. Comput. Chem. 1993, 14, 1504.
55. (a) Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211.
56. (b) Reed, A. E.; Weinhold, F. J. Chem. Phys. 1985, 83, 1736.
57. (c) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
58. (d) Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
59. Kohn, W.; Becke, A. D.; Parr, R. G. J. Phys. Chem. 1996, 100, 12974.
60. For several recent papers reported combined B3LYP and NBO studies, see, for example: (a) Glendening, E. D.; Hrabal, J. A. J. Am. Chem. Soc. 1997, 119, 12940. (b) Krapp, J.; Remko, M.; Schleyer, P. v. R. Inorg. Chem. 1997, 36, 4241. (c) García, A.; Cruz, E. M.; Sarasola, C.; Ugalde, J. M. J. Phys. Chem. A 1997, 101, 3021.
61. For several recent papers reported combined B3LYP and NBO studies, see, for example: (a) Glendening, E. D.; Hrabal, J. A. J. Am. Chem. Soc. 1997, 119, 12940. (b) Krapp, J.; Remko, M.; Schleyer, P. v. R. Inorg. Chem. 1997, 36, 4241. (c) García, A.; Cruz, E. M.; Sarasola, C.; Ugalde, J. M. J. Phys. Chem. A 1997, 101, 3021.
62. For several recent papers reported combined B3LYP and NBO studies, see, for example: (a) Glendening, E. D.; Hrabal, J. A. J. Am. Chem. Soc. 1997, 119, 12940. (b) Krapp, J.; Remko, M.; Schleyer, P. v. R. Inorg. Chem. 1997, 36, 4241. (c) García, A.; Cruz, E. M.; Sarasola, C.; Ugalde, J. M. J. Phys. Chem. A 1997, 101, 3021.
63. (a) Wiberg, K. B.; Castejon, H.; Keith, T. A. J. Comput. Chem. 1996, 17, 185.
64. (b) Wiberg, K. B.; Keith, T. A.; Frisch, M. J.; Murcko, M. J. Phys. Chem. 1995, 99, 9073.
65. (c) Wiberg, K. B.; Rablen, P. R.; Rush, D. J.; Keith, T. A. J. Am. Chem. Soc. 1995, 117, 4261.
66. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; VCH Publishers: Weinheim, 1990.
67. Schaftenaar, G. MOLDEN-A Package for Displaying Molecular Density; CAOS/CAMM Center Nijmegen: Toernooiveld, Nijmegen, The Nederlands, 1991.
68. (a) Guerra, A.; Lunazzi, L. J. Org. Chem. 1995, 60, 7959.
69. (b) Warren, C. H.; Wettermark, G.; Weis, K. J. Am. Chem. Soc. 1971, 93, 4658.
70. (c) Patai, S., Ed. The Chemistry of the Carbon-Nitrogen Double Bond; Wiley: New York, 1970.
71. (a) Taft, R. W.; Lewis, I. C. J. Am. Chem. Soc. 1958, 80, 2436.
72. (b) Ehrenson, S.; Brownlee, R. T. C.; Taft, R. W. Prog. Phys. Org. Chem. 1973, 10, 1.
73. Streitwieser, A.; Choy, G. S.-C.; Abu-Hasanayn, F. J. Am. Chem. Soc. 1997, 119, 5013.
74. Bader, R. F. W. Can. J. Chem. 1986, 64, 1036.
75. Quite recently, Bose et al. have reported that in the microwave-assisted reaction between acyl chlorides and imines the amount of trans cycloadducts is usually larger that that obtained under classical thermal conditions. A possible explanation for this result is that under microwave irradiation the route involving direct reaction between the acyl chloride and the imine competes more efficiently with the keteneimine reaction path. See: Bose, A. K.; Banik, B. K.; Manhas, M. S. Tetrahedron Lett. 1995, 36, 213. See also: Bose, A. K.; Sayaraman, M.; Okawa, A.; Bari, S. S.; Robb, E. W.; Manhas, M. S. Tetrahedron Lett. 1996, 37, 6989.
76. Quite recently, Bose et al. have reported that in the microwave-assisted reaction between acyl chlorides and imines the amount of trans cycloadducts is usually larger that that obtained under classical thermal conditions. A possible explanation for this result is that under microwave irradiation the route involving direct reaction between the acyl chloride and the imine competes more efficiently with the keteneimine reaction path. See: Bose, A. K.; Banik, B. K.; Manhas, M. S. Tetrahedron Lett. 1995, 36, 213. See also: Bose, A. K.; Sayaraman, M.; Okawa, A.; Bari, S. S.; Robb, E. W.; Manhas, M. S. Tetrahedron Lett. 1996, 37, 6989.