Selective synthesis of nonracemic 3-pyrrolines and 2,3-cis-2- vinylaziridines from (Z)-amino allylic alcohols: A new synthetic route to chiral 3,4-dehydroproline

Synlett

Volumn , Issue 2, 1999, Pages 228-230

  Ishii, Kiyonori ^a   Ohno, Hiroaki ^a   Takemoto, Yoshiji ^a   Ibuka, Toshiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

3,4 dehydroproline; 3 pyrroline; Aziridine; Thermodynamic equilibration

Indexed keywords

AMINOALCOHOL; AZIRIDINE DERIVATIVE; PROLINE DERIVATIVE; PYRROLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; STEREOCHEMISTRY; SYNTHESIS; THERMODYNAMICS;

EID: 0032912089     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2589     Document Type: Article

References (32)

1. (a) Barsky, S. H.; Gopalakrishna, R. Cancer Res. 1987, 47, 1663.
2. (b) Leu. R. W.; Stewart, C. A.; Herriott, M. J.; Fast, D. J.; Rummage, J. A. Immunobiology 1993, 188, 242.
3. (c) Sullivan, T. A.; Uschmann, B.; Hough, R.; Leboy, P. S. J. Biol. Chem. 1994, 269, 22500.
4. (d) Jiang, H; Zhou, A.; Herriott, M. J.; Rummage, J. A.; Stewart, C. A.; Fast, D. J.; Leu, R. W. Scand. J. Immunol. 1996, 44, 101.
5. (a) Hardy, P. M.; Sheppard, P. W. J. Chem. Soc. Perkin Trans. 1 1983, 723.
6. (b) Amoscato, A. A.; Babcock, G. F.; Nishioka, K. Peptides 1984, 5, 489.
7. (c) Tzougraki, C.; Dairman, W. M.; Makofske, R. C.; Aeppli, L.; Meienhofer, J. Int. J. Peptide Protein Res. 1986, 28, 370.
8. (d) Johnson, R. L.; Rajakumar, G.; Yu, K.-L.; Mishra, R. K. J. Med. Chem. 1986, 29, 2104.
9. (a) Baldwin, J. E.; Field, R. A.; Lawrence, C. C.; Lee, V.; Robinson, J. K.; Schofield, C. J. Tetrahedron Lett. 1994, 35, 4649.
10. (b) Robinson, J. K.; Lee, V.; Claridge, T. D. W.; Baldwin, J. E.; Schofield, C. J. Tetrahedron 1998, 54, 981.
11. (a) Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859.
12. (b) Chung, J. Y. L.; Wasicak, J. T.; Arnold, W. A.; May, C. S.; Nadzan, A. M.; Holladay, M. W. J. Org. Chem. 1990, 55, 270.
13. (c) Holladay, M. W.; Lin, C. W.; May, C. S.; Garvey, D. S.; Witte, D. G.; Miller, T. R.; Wolfram, C. A. W.; Nadzan, A. M. J. Med. Chem. 1991, 34, 455.
14. Jegham, S.; Das, B. C. Tetrahedron Lett. 1988, 29, 4419.
15. (a) Burley, I.; Hewson, A. T. Tetrahedron Lett. 1994, 35, 7099.
16. (b) Horikawa, M.; Shirahama, H. Synlett 1996, 95.
17. (c) Sibi, M. P.; Christensen, J. W. Tetrahedron Lett. 1995, 36, 6213.
18. (a) Dormoy, J.-R.; Castro, B.; Chappuis, G.; Fritschi, U. S.; Grogg, P. Angew. Chem. Int. Ed. Engl. 1980, 19, 742.
19. (b) Rüeger, H.; Benn, M. H. Can. J. Chem. 1982, 60, 2918.
20. (c) Remuzon, P. Tetrahedron 1996, 52, 13803.
21. (d) Koskinen, A. M. P.; Schwerdtfeger, J.; Edmonds, M. Tetrahedron Lett. 1997, 38, 5399.
22. (e) Schumacher, K. K.; Jiang, J.; Joullié, M. M. Tetrahedron: Asymmetry 1998, 9, 47.
23. (a) Robertson, A. V.; Witkop, B. J. Am. Chem. Soc. 1962, 84, 1697.
24. (b) Schieweck, F.; Altenbach, H.-J. Tetrahedron: Asymmetry 1998, 9, 403.
25. (a) Ohno, H.; Ishii, K.; Honda, A.; Tamamura, H.; Fujii, N.; Takemoto, Y.; Ibuka, T. J. Chem. Soc., Perkin Trans I 1998, 3703.
26. (b) Ohno, H.; Toda, A.; Fujii, N.; Ibuka, T. Tetrahedron: Asymmetry 1998, in print.
27. (a) Ando, K. Tetrahedron Lett. 1995, 36, 4105.
28. 2NEt according to the protocol of Blanchette; see, Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183.
29. 2NEt according to the protocol of Blanchette; see, Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183.
30. (a) Mimura, N.; Ibuka, T.; Akaji, M.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Chem. Commun. 1996, 351.
31. (b) Ibuka, T.; Mimura, N.; Aoyama, H.; Akaji, M.; Ohno, H.; Miwa, Y.; Taga, T.; Nakai, K.; Tamamura, H.; Fujii, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 999.
32. The mesylate 19 was used without purification for the next step due to its poor stability.