Palladium(0)-Catalyzed Isomerization Reactions of Aziridines Bearing an α,β-Unsaturated Ester Group: A Thermodynamic Preference for Chiral Alkyl (2E)-4,5-cis-4,5-Epimino-N-(alkyl- or arylsvdfonyl) 2-Enoates over the Other Three Stereoisomers

Journal of Organic Chemistry

Volumn 62, Issue 9, 1997, Pages 2982-2991

  Ibuka, Toshiro ^a   Mimura, Norio ^a   Ohno, Hiroaki ^a   Nakai, Kazuo ^a   Akaji, Masako ^a   Habashita, Hiromu ^a   Tamamura, Hirokazu ^a   Miwa, Yoshihisa ^a   Taga, Tooru ^a   Fujii, Nobutaka ^a   Yamamoto, Yoshinori ^b  

^a KYOTO UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000831199     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962094u     Document Type: Article

References (57)

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2. According to IUPAC rules, the structure inside the bracket following ψ is the unit substituting for the amide bond. For nomenclature, see: IUPAC-IUB Joint Commission on Biochemical Nomenclature Eur. J. Biochem. 1984, 138, 9. Spatola, A. In Chemistry and Biochemistry of Amino Acids, Peptides and Proteins; Weinstein, B., Ed.; Marcel Dekker: New York, 1983; pp 267-358.
3. (a) For a review of syntheses of (E)-alkene dipeptide isosteres up to May 1992, see: Ibuka, T. J. Synth. Org. Chem. Jpn. 1992, 50, 953. (b) Bol, K. M.; Liskamp, R. M. J. Tetrahedron 1992, 31, 6425. (c) Li, Y.-L.; Luthman, K.; Hacksell, U. Tetrahedron Lett. 1992, 33, 4487. (d) Ibuka, T.; Yamamoto, Y. Synlett 1992, 760. (e) Ibuka, T.; Taga, T.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Chounan, Y.; Nemoto, H.; Yamamoto, Y. J. Org. Chem. 1993, 58, 1207. (f) Bohnstedt, A. C.; Prasad, J. V. N. V.; Rich, D. H. Tetrahedron Lett. 1993, 34, 5217. (g) Yong, Y. F.; Lipton, M. A. Bioorg. Med. Chem. Lett. 1993, 3, 2879. (h) Fujii, N.; Nakai, K.; Habashita, H.; Yoshizawa, H.; Ibuka, T.; Garrido, F.; Mann, A.; Chounan, Y.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 4227. (i) Ibuka, T.; Nakai, K.; Habashita, H.; Bessho, K.; Fujii, N.; Chounan, Y.; Yamamoto, Y. Tetrahedron 1993, 49, 9479.
4. (a) For a review of syntheses of (E)-alkene dipeptide isosteres up to May 1992, see: Ibuka, T. J. Synth. Org. Chem. Jpn. 1992, 50, 953. (b) Bol, K. M.; Liskamp, R. M. J. Tetrahedron 1992, 31, 6425. (c) Li, Y.-L.; Luthman, K.; Hacksell, U. Tetrahedron Lett. 1992, 33, 4487. (d) Ibuka, T.; Yamamoto, Y. Synlett 1992, 760. (e) Ibuka, T.; Taga, T.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Chounan, Y.; Nemoto, H.; Yamamoto, Y. J. Org. Chem. 1993, 58, 1207. (f) Bohnstedt, A. C.; Prasad, J. V. N. V.; Rich, D. H. Tetrahedron Lett. 1993, 34, 5217. (g) Yong, Y. F.; Lipton, M. A. Bioorg. Med. Chem. Lett. 1993, 3, 2879. (h) Fujii, N.; Nakai, K.; Habashita, H.; Yoshizawa, H.; Ibuka, T.; Garrido, F.; Mann, A.; Chounan, Y.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 4227. (i) Ibuka, T.; Nakai, K.; Habashita, H.; Bessho, K.; Fujii, N.; Chounan, Y.; Yamamoto, Y. Tetrahedron 1993, 49, 9479.
5. (a) For a review of syntheses of (E)-alkene dipeptide isosteres up to May 1992, see: Ibuka, T. J. Synth. Org. Chem. Jpn. 1992, 50, 953. (b) Bol, K. M.; Liskamp, R. M. J. Tetrahedron 1992, 31, 6425. (c) Li, Y.-L.; Luthman, K.; Hacksell, U. Tetrahedron Lett. 1992, 33, 4487. (d) Ibuka, T.; Yamamoto, Y. Synlett 1992, 760. (e) Ibuka, T.; Taga, T.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Chounan, Y.; Nemoto, H.; Yamamoto, Y. J. Org. Chem. 1993, 58, 1207. (f) Bohnstedt, A. C.; Prasad, J. V. N. V.; Rich, D. H. Tetrahedron Lett. 1993, 34, 5217. (g) Yong, Y. F.; Lipton, M. A. Bioorg. Med. Chem. Lett. 1993, 3, 2879. (h) Fujii, N.; Nakai, K.; Habashita, H.; Yoshizawa, H.; Ibuka, T.; Garrido, F.; Mann, A.; Chounan, Y.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 4227. (i) Ibuka, T.; Nakai, K.; Habashita, H.; Bessho, K.; Fujii, N.; Chounan, Y.; Yamamoto, Y. Tetrahedron 1993, 49, 9479.
6. (a) For a review of syntheses of (E)-alkene dipeptide isosteres up to May 1992, see: Ibuka, T. J. Synth. Org. Chem. Jpn. 1992, 50, 953. (b) Bol, K. M.; Liskamp, R. M. J. Tetrahedron 1992, 31, 6425. (c) Li, Y.-L.; Luthman, K.; Hacksell, U. Tetrahedron Lett. 1992, 33, 4487. (d) Ibuka, T.; Yamamoto, Y. Synlett 1992, 760. (e) Ibuka, T.; Taga, T.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Chounan, Y.; Nemoto, H.; Yamamoto, Y. J. Org. Chem. 1993, 58, 1207. (f) Bohnstedt, A. C.; Prasad, J. V. N. V.; Rich, D. H. Tetrahedron Lett. 1993, 34, 5217. (g) Yong, Y. F.; Lipton, M. A. Bioorg. Med. Chem. Lett. 1993, 3, 2879. (h) Fujii, N.; Nakai, K.; Habashita, H.; Yoshizawa, H.; Ibuka, T.; Garrido, F.; Mann, A.; Chounan, Y.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 4227. (i) Ibuka, T.; Nakai, K.; Habashita, H.; Bessho, K.; Fujii, N.; Chounan, Y.; Yamamoto, Y. Tetrahedron 1993, 49, 9479.
7. (a) For a review of syntheses of (E)-alkene dipeptide isosteres up to May 1992, see: Ibuka, T. J. Synth. Org. Chem. Jpn. 1992, 50, 953. (b) Bol, K. M.; Liskamp, R. M. J. Tetrahedron 1992, 31, 6425. (c) Li, Y.-L.; Luthman, K.; Hacksell, U. Tetrahedron Lett. 1992, 33, 4487. (d) Ibuka, T.; Yamamoto, Y. Synlett 1992, 760. (e) Ibuka, T.; Taga, T.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Chounan, Y.; Nemoto, H.; Yamamoto, Y. J. Org. Chem. 1993, 58, 1207. (f) Bohnstedt, A. C.; Prasad, J. V. N. V.; Rich, D. H. Tetrahedron Lett. 1993, 34, 5217. (g) Yong, Y. F.; Lipton, M. A. Bioorg. Med. Chem. Lett. 1993, 3, 2879. (h) Fujii, N.; Nakai, K.; Habashita, H.; Yoshizawa, H.; Ibuka, T.; Garrido, F.; Mann, A.; Chounan, Y.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 4227. (i) Ibuka, T.; Nakai, K.; Habashita, H.; Bessho, K.; Fujii, N.; Chounan, Y.; Yamamoto, Y. Tetrahedron 1993, 49, 9479.
8. (a) For a review of syntheses of (E)-alkene dipeptide isosteres up to May 1992, see: Ibuka, T. J. Synth. Org. Chem. Jpn. 1992, 50, 953. (b) Bol, K. M.; Liskamp, R. M. J. Tetrahedron 1992, 31, 6425. (c) Li, Y.-L.; Luthman, K.; Hacksell, U. Tetrahedron Lett. 1992, 33, 4487. (d) Ibuka, T.; Yamamoto, Y. Synlett 1992, 760. (e) Ibuka, T.; Taga, T.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Chounan, Y.; Nemoto, H.; Yamamoto, Y. J. Org. Chem. 1993, 58, 1207. (f) Bohnstedt, A. C.; Prasad, J. V. N. V.; Rich, D. H. Tetrahedron Lett. 1993, 34, 5217. (g) Yong, Y. F.; Lipton, M. A. Bioorg. Med. Chem. Lett. 1993, 3, 2879. (h) Fujii, N.; Nakai, K.; Habashita, H.; Yoshizawa, H.; Ibuka, T.; Garrido, F.; Mann, A.; Chounan, Y.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 4227. (i) Ibuka, T.; Nakai, K.; Habashita, H.; Bessho, K.; Fujii, N.; Chounan, Y.; Yamamoto, Y. Tetrahedron 1993, 49, 9479.
9. (a) For a review of syntheses of (E)-alkene dipeptide isosteres up to May 1992, see: Ibuka, T. J. Synth. Org. Chem. Jpn. 1992, 50, 953. (b) Bol, K. M.; Liskamp, R. M. J. Tetrahedron 1992, 31, 6425. (c) Li, Y.-L.; Luthman, K.; Hacksell, U. Tetrahedron Lett. 1992, 33, 4487. (d) Ibuka, T.; Yamamoto, Y. Synlett 1992, 760. (e) Ibuka, T.; Taga, T.; Habashita, H.; Nakai, K.; Tamamura, H.; Fujii, N.; Chounan, Y.; Nemoto, H.; Yamamoto, Y. J. Org. Chem. 1993, 58, 1207. (f) Bohnstedt, A. C.; Prasad, J. V. N. V.; Rich, D. H. Tetrahedron Lett. 1993, 34, 5217. (g) Yong, Y. F.; Lipton, M. A. Bioorg. Med. Chem. Lett. 1993, 3, 2879. (h) Fujii, N.; Nakai, K.; Habashita, H.; Yoshizawa, H.; Ibuka, T.; Garrido, F.; Mann, A.; Chounan, Y.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 4227. (i) Ibuka, T.; Nakai, K.; Habashita, H.; Bessho, K.; Fujii, N.; Chounan, Y.; Yamamoto, Y. Tetrahedron 1993, 49, 9479.
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55. For the PM3 level of theory, see: Stewart, J. J. P. J. Comput. Chem. 1989, 10, 210. All optimizations were carried out by using the PM3 method, and stationary points were also confirmed by vibrational analysis on the PM3 potential surface. Single-point energy calculations were done at the HF/3-21G** and HF/4-31G** levels of theory. All calculations were performed using the program GAUSSIAN 92 on a CRAY Y-MP2E/264 at the Supercomputer Laboratory, Institute for Chemical Research, Kyoto University. GAUSSIAN 92, Revision C: Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Forseman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian Inc., Pittsburgh, PA, 1992.
56. For the PM3 level of theory, see: Stewart, J. J. P. J. Comput. Chem. 1989, 10, 210. All optimizations were carried out by using the PM3 method, and stationary points were also confirmed by vibrational analysis on the PM3 potential surface. Single-point energy calculations were done at the HF/3-21G** and HF/4-31G** levels of theory. All calculations were performed using the program GAUSSIAN 92 on a CRAY Y-MP2E/264 at the Supercomputer Laboratory, Institute for Chemical Research, Kyoto University. GAUSSIAN 92, Revision C: Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Forseman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian Inc., Pittsburgh, PA, 1992.
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