Do reaction conditions affect the stereoselectivity in the staudinger reaction?

Journal of Organic Chemistry

Volumn 71, Issue 18, 2006, Pages 6983-6990

  Wang, Yikai ^a   Liang, Yong ^a   Jiao, Lei ^a   Du, Da Ming ^a   Xu, Jiaxi ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; NITROGEN COMPOUNDS; REACTION KINETICS;

ACYL CHLORIDES; LACTAMS; STAUDINGER REACTION; STEREOSELECTIVITY-CONTROLLING FACTORS;

STEREOCHEMISTRY;

BETA LACTAM DERIVATIVE; CHLORIDE; IMINE; KETENE DERIVATIVE; REAGENT; SOLVENT; TERTIARY AMINE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STAUDINGER REACTION; STEREOCHEMISTRY;

AMINES; CHEMISTRY, ORGANIC; CHLORIDES; ETHYLENES; IMINES; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; SOLVENTS; STEREOISOMERISM;

EID: 33750476638     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0611521     Document Type: Article

References (64)

1. For recent reviews on syntheses of β-lactam. see: (a) Van der Steen, F. H.; van Koten, G. Tetrahedron 1991, 47, 7503-7524.
2. (b) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Eur. J. Org. Chem. 1999, 3223-3235.
3. (c) Singh, G. S. Tetrahedron 2003, 59, 7631-7649.
4. (d) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Curr. Med. Chem. 2004, 11, 1837-1879.
5. For a review, see: The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; Verlag Chemie: New York, 1993.
6. (a) Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982; Vols. 1-3.
7. (b) Southgate, R.; Branch, C.; Coulton, S.; Hunt, E. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Luckacs, G., Ed.; Springer-Verlag: Berlin, 1993; Vol. 2, p 621.
8. (c) Southgate, R. Contemp. Org. Synth. 1994, 1, 417.
9. (a) Banik, B. K.; Becker, F. F.; Banik, I. Bioorg. Med. Chem. 2004, 12, 2523-2528.
10. (b) Banik, B. K.; Banik, I.; Becker, F. F. Bioorg. Med. Chem. 2005, 13, 3611-3622.
11. (c) Rothstein, J. D.; Patel, S.; Regan, M. R.; Haenggeli, C.; Huang, Y. H.; Bergles, D. E.; Jin, L.; Hoberg, M. D.; Vidensky, S.; Chung, D. S.; Toan, S. V.; Bruijn, L. I.; Su, Z. Z.; Gupta, P.; Fisher, P. B. Nature 2005, 433, 73-77.
12. (d) Miller, T. M.; Cleveland, D. W. Science 2005, 307, 361-362.
13. Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams: Georg, G. I., Ed.: Verlag Chemie: New York. 1993; pp 295-368 and references therein.
14. (a) Bose, A. K.; Anjaneyulu, B.; Bhattacharya, S. K.; Manhas, M. S. Tetrahedron 1967, 23, 4769-4776.
15. (b) Duran, F.; Ghosez, L. Tetrahedron Lett. 1970, 11, 245-248.
16. (c) Bose, A. K.; Spiegelman, G.; Manhas, M. S. Tetrahedron Lett. 1971, 12, 3167-3170.
17. (d) Bose, A. K.; Chiang, Y. H. Manhas, M. S. Tetrahedron Lett. 1972, 13, 4091-4094.
18. (e) Nelson, D. A. J. Org. Chem. 1972, 37, 1447-1449.
19. (f) Moore, H. W.; Hernandez, L., Jr. Chambers, R. J. Am. Chem. Soc. 1978, 100, 2245-2247.
20. (g) Pacansky, J. Chang, J. S.; Brown, D. W.; Schwarz, W. J. Org. Chem. 1982, 47, 2233-2234.
21. (h) Moore, H. W.; Hughes, G.; Srinivasachar, K.; Fernandez, M.; Nguyen, N. V.; Schoon, D.; Tranne, A. J. Org. Chem. 1985, 50, 4231-4238.
22. (i) Brady, W. T.; Gu, Y. Q. J. Org. Chem. 1989, 54, 2838-2842.
23. (j) Lynch, J. F.; Riseman, S. M.; Laswell, W. L.; Tschaen, D. M.; Volante, R.; Smith, G. B.; Shinkai, I. J. Org. Chem. 1989, 54, 3792-3796.
24. (k) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784-5791.
25. (l) Georg, G. I.; He, P.; Kant, J.; Wu, Z. J. J. Org. Chem. 1993, 58, 5771-5778.
26. (m) Panunzio, M.; Bacchi, S.; Campana, F.; Fiume, L.; Vicennati, P. Tetrahedron Lett. 1999, 40, 8495-8498.
27. (n) Alcaide, B.; Almendros, P.; Salgado, N. R.; Rodriguez-Vicente, A. J. Org. Chem. 2000, 65, 4453-4455.
28. (a) Sordo, J. A.; González, J.; Sordo, T. L. J. Am. Chem. Soc. 1992, 114, 6249-6251.
29. (b) Cossio, F. P.; Ugalde, J. M.; Lopez, X.; Lecea, B.; Palomo, C. J. Am. Chem. Soc. 1993, 115, 995-1004.
30. (c) Arrieta, A.; Ugalde, J. M.; Cossio, F. P. Tetrahedron Lett. 1994, 35, 4465-4468.
31. (d) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085-2093.
32. (e) Arrieta, A.; Lecea, B.; Cossio, F. P. J. Org. Chem. 1998, 63, 5869-5876.
33. (f) Arrieta, A.; Cossio, F. P.; Fernandez, I.; Gomez-Gallego, M.; Lecea, B.; Mancheno, M. J.; Sierra, M. A. J. Am. Chem. Soc. 2000, 122, 11509-11510.
34. (g) Bongini, A.; Panunzio, M.; Piersanti, G.; Bandini, E.; Martelli, G.; Spunta, G.; Venturini, A. Eur. J. Org. Chem. 2000, 2379-2390.
35. (h) Arrieta, A.; Cossio, F. P.; Lecea, B. J. Org. Chem. 2000, 65, 8458-8464.
36. (i) Zhou, C.; Birney, D. M. J. Am. Chem. Soc. 2002, 124, 5231-5241.
37. (j) Venturini, A.; González, J. J. Org. Chem. 2002, 67, 9089-9092.
38. (k) Campomanes, P.; Menendez, M. I.; Sordo, T. L. J. Phys. Chem. A 2005, 109, 11022-11026.
39. Jiao, L.; Liang, Y.; Xu, J. X. J. Am. Chem. Soc. 2006, 128, 6060-6069.
40. (a) Sheehan, J. C.; Buhle, E. L.; Corey, E. J.; Lanbach, G. D.; Ryan, J. J. J. Am. Chem. Soc. 1950, 72, 3828-3829.
41. (b) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1985, 26, 3783-3786.
42. (c) Evans, D. A.; Williams, J. M. Tetrahedron Lett. 1988, 29, 5065-5068.
43. (d) Xu, J. X.; Zuo, G.; Chan, W. L. Heteroat. Chem. 2001, 12, 636-640.
44. (e) Xu, J. X.; Zuo, G.; Zhang, Q. H.; Chan, W. L. Heteroat. Chem. 2002, 13, 276-279.
45. (f) Huang, X.; Xu, J. X. Heteroat. Chem. 2003, 14, 564-569.
46. (g) Xu, J. X.; Wang, C.; Zhang, Q. H. Chin. J. Chem. 2004, 22, 1012-1018.
47. (a) McGuire, M. A.; Hegedus, L. S. J. Am. Chem. Soc. 1982, 104, 5538-5540.
48. (b) Hegedus, L. S.; Imwinkelried, R.; Aland-Sargent, M.; Dvorak, D.; Satoh, Y. J. Am. Chem. Soc. 1990, 112, 1109-1117.
49. (c) Hegedus, L. S. Tetrahedron 1997, 53, 4105-4128.
50. (a) Podlech, J.; Linder, M. R. J. Org. Chem. 1997, 62, 5873-5883.
51. (b) Linder, M. R.; Podlech, J. Org. Lett. 1999, 1, 869-871.
52. (c) Lawlor, M. D.; Lee, T. W.; Danheiser, R. L. J. Org. Chem. 2000, 65, 4375-4384.
53. (d) Linder, M. R.; Frey, W. U.; Podlech, J. J. Chem. Soc., Perkin Trans. 1 2001, 2566-2577.
54. (e) Linder, M. R.; Podlech, J. Org. Lett. 2001, 3, 1849-1851.
55. (f) Liang, Y.; Jiao, L.; Zhang, S. W.; Xu, J. X. J. Org. Chem. 2005, 70, 334-337.
56. (g) Jiao, L.; Zhang, Q. F.; Liang, Y.; Zhang, S. W.; Xu, J. X. J. Org. Chem. 2006, 71, 815-818.
57. (h) Jiao, L.; Liang, Y.; Zhang, Q. F.; Zhang, S. W.; Xu, J. X. Synthesis 2006, 659-665.
58. (a) Palomo, C.; Cossio, F. P.; Odriozola, J. M.; Oiarbide, M.; Ontoria, J. M. Tetrahedron Lett. 1989, 30, 4577-4580.
59. (b) Browne, M.; Burnett, D. A.; Caplen, M. A.; Chen, L. Y.; Clader, J. W.; Domalski, M.; Dugar, S.; Pushpavanam, P.; Sher, R.; Vaccaro, W.; Viziano, M.; Zhao, H. Tetrahedron Lett. 1995, 36, 2555-2558.
60. Staudinger, H. Justus Liebigs Ann. Chem. 1907, 356, 51-123.
61. 1H NMR spectra of crude reaction mixtures.
62. The Hammett constants (σ) cited are all taken from: Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
63. 2COCl 6e to imine 2a was 1.3:1.0, ratios of 13a:14a were obtained in 80:20, 84: 16, 85:15, 84:16, and 78:22, respectively, in the presence of 1.0, 1.3, 1.5, 2.0, and 2.6 equiv of triethylamine. On the basis of the above results, the amount of triethylamine does not affect the ratio of products obviously.
64. Jiao, L.; Liang, Y.; Wu, C. Z.; Huang, X.; Xu, J. X. Chem. Res. Chin. Univ. 2005, 21, 59-64.