(Z)-selective β-bromination of N-formyl-α,β-dehydroamino acid esters

Tetrahedron

Volumn 52, Issue 16, 1996, Pages 5751-5764

  Yamada, Masaki ^a   Nakao, Kazuya ^a   Fukui, Toshio ^a   Nunami, Ken Ichi ^a  

^a MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; ORGANOBROMINE DERIVATIVE;

ARTICLE; BROMINATION; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029878816     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00209-8     Document Type: Article

References (56)

1. Nunami, K.; Hiramatsu, K.; Hayashi, K.; Matsumoto, K. Tetrahedron 1988, 44, 5467.
2. (a) Hiramatsu, K.; Nunami, K.; Hayashi, K.; Matsumoto, K. Synthesis 1990, 781.
3. (b) Nunami, K.; Yamada, M.; Fukui, T.; Matsumoto, K. J. Org. Chem. 1994, 59, 7635.
4. (c) Yamada, M.; Fukui, T.; Nunami, K. Synthesis 1995, 1365..
5. Yamada, M.; Fukui, T.; Nunami, K. Tetrahedron Lett. 1995, 36, 257.
6. (a) van Leusen, A. M.; Wildeman, J.; Oldenziel, O. H. J. Org. Chem. 1977, 42, 1153.
7. (b) Lantos, I.; Zhang, W-Y.; Shui, X.; Eggleston, D. S. J. Org. Chem. 1993, 58, 7092.
8. Das, J.; Reid, J. A.; Kronenthal, D. R.; Singh, J.; Pansegrau, P. D.; Mueller, R. H. Tetrahedron Lett. 1992, 33, 7835.
9. 1H-NMR spectra. The ester protons of the main products resonated upfield (δ = 3.96-4.00 ppm) relative to those of the corresponding E-isomers (δ = 4.35 ppm) and imines (δ = 4.20-4.33 ppm), because of the shielding anisotropic effect of the adjacent benzene ring. Danion-Bougot, R.; Danion, D.; Francis, G. Tetrahedron Lett. 1990, 31, 3739.
10. 2 afforded the corresponding E-and Z-vinyl chlorides in a 20:80 E/Z ratio with DABCO and in a 10:90 E/Z ratio with DBU or t-BuOK as a base. They described the switched ratio (90:10 E/Z) in the text, but we consider that the ratio (10:90 E/Z) in their experimental section is correct as judged by the experimental data. Kolar, A. J.; Olsen, R. K. J. Org. Chem. 1980, 45, 3246.
11. 10 indicated that the product should be Z-isomer. Bland, J.; Shah, A.; Bortolussi, A.; Stammer, C. H. J. Org. Chem. 1988, 53, 992.
12. Olsen, R. K.; Hennen, W. J.; Wardke, R. B. J. Org. Chem. 1982, 47, 4605.
13. Shin, C.; Sato, Y.; Ohmatsu, H.; Yoshimura, J. Bull. Chem. Soc. Jpn. 1981, 54, 1137.
14. Richards, K. D.; Kolar, A. J.; Srinivasan, A.; Stephenson, R. W.; Olsen, R. K. J. Org. Chem. 1976, 41, 3674.
15. Nakatsuka, S.; Tanino, H.; Kishi, Y. J. Am. Chem. Soc. 1975, 97, 5010.
16. Combs, A. P.; Armstrong, R. W. Tetrahedron Lett. 1992, 33, 6419.
17. Coleman, R. S.; Carpenter, A. J. J. Org. Chem. 1992, 57, 5813.
18. Armstrong, R. W.; Moran, E. J. J. Am. Chem. Soc. 1992, 114, 371.
19. Armstrong, R. W.; Tellew, J. E.; Moran, E. J. J. Org. Chem. 1992, 57, 2208.
20. Coleman, R. S.; Carpenter, A. J. J. Org. Chem. 1993, 58, 4452.
21. (a) Suzuki, M.; Nunami, K.; Moriya, T.; Matsumoto, K.; Yoneda, N. J. Org. Chem. 1978, 43, 4933.
22. (b) Suzuki, M.; Nunami, K.; Matsumoto, K.; Yoneda, N.; Kasuga, O.; Yoshida, H.; Yamaguchi, T. Chem. Pharm. Bull. 1980, 28, 2374.
23. (c) Nunami, K.; Suzuki, M.; Yoneda, N. Chem. Pharm. Bull. 1982, 30, 4015.
24. (d) Schöllkopf, U.; Gerhart, F.; Schröder, R.; Hoppe, D. Liebigs Ann. Chem. 1972, 766, 116.
25. Chevallet, P.; Garrouste, P.; Malawska, B.; Martinez, J. Tetrahedron Lett. 1993, 34, 7409.
26. 13
27. α-Bromoimines 10 were isolated as a stable intermediate by a normal work-up. See experimental section.
28. 14
29. The orbital overlap of the aromatic π-system with the developing p-orbital and with the resulting olefin might perturb the transition state and the ground state energies, respectively.
30. (a) Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1988, 159 and references cited therein.
31. (b) Olsen, R. K.; Kolar, A. J. Synthesis 1977, 457.
32. Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1984, 53.
33. (a) Fife, T. H.; Przystas, T. J.; Pujari, M. P. J. Am. Chem. Soc. 1988, 110, 8157.
34. (b) Barluenga, J.; Ferrero, M.; Palacios, F. Tetrahedron Lett. 1990, 34, 3497.
35. 27
36. (a) Kolar, A.; Olsen, R. J. Org. Chem. 1980, 45, 3246.
37. (b) Srinivasan, A.; Richards, K. D.; Olsen, R. K. Tetrahedron Lett. 1976, 891.
38. (c) Rich, D. H.; Tam, J.; Mathiaparanan, P.; Grant, J. Synthesis 1975, 402.
39. (d) Brown, A. G.; Smake, T. C. J. Chem. Soc., Chem. Commun. 1969, 1489.
40. 13C-NMR and NOE studies were carried out with 10a,b,d, the data were not obtained enough for the determination of syn-and anti-isomers of α-bromoimines 10. (a) Hoffmann, W. R. Chem. Rev. 1989, 89, 1841.
41. (b) Overberger, C. G.; Marullo, N. P.; Hiskey, R. G. J. Am. Chem. Soc. 1961, 83, 1374.
42. Calculations were carried out with IRIS 4D/35. Optimized structures were obtained using AMI hamiltonian (MOPAC 6.0).
43. (a) Cram, D. J.; Uyeda, R. T. J. Am. Chem. Soc. 1964, 86, 5466.
44. (b) Bank, S.; Rowe Jr., C. A.; Schriesheim, A. J. Am. Chem. Soc. 1963, 85, 2115.
45. (c) Doering, W. E.; Gaspar, P. P. J. Am. Chem. Soc. 1963, 85, 3043.
46. 17 which indicates the intramolecular hydrogen transfer in the bromination. The geometric structure of olefine product was affected by the chirality of the α-position of the imine.
47. (a) Almy, J.; Cram, D. J. J. Am. Chem. Soc. 1969, 91, 4459.
48. (b) Hussenius, A.; Matsson, O.; Bergson, G. J. Chem. Soc., Perkin Trans. II 1989, 851.
49. (c) Cram D. J.; Ford, W. T.; Gosser, L. J. Am. Chem. Soc. 1968, 90, 2598.
50. (d) Ford, W. T.; Cram, D. J. J. Am. Chem. Soc. 1968, 90, 2606.
51. (e) Ford, W. T.; Cram, D. J. J. Am. Chem. Soc. 1968, 90, 2612.
52. (f) Wong, S. M.; Fischer, H. P.; Cram, D. J. J. Am. Chem. Soc. 1971, 93, 2235.
53. Though Coleman and Carpenter, on the other hand, reported that the ground state rotamer leading to the E-product is more stable than that leading to the Z-product, N-and β-substituents of their substrate and molecular mechanics calculations were not specified. We believe that this discrepancy is due to the substituents at the N-and β-positions which synergetically contributed to the potential energy of their ground-state conformers.
54. 30c
55. 32 in which the formyl carbonyl group interacted with the hydrogen, and the steric repulsion would be amplified in the transition state.
56. Rotational isomer about the N-formylamine.