A new synthesis of aziridine-2-carboxylates by reaction of hexahydro-1,3,5-triazines with alkyldiazoacetates in the presence of tin(IV) chloride

Tetrahedron Letters

Volumn 37, Issue 39, 1996, Pages 7069-7070

  Ha, Hyun Joon ^a   Kang, Kyung Ho ^a   Suh, Jang Min ^a   Ahn, Young Gil ^a  

^a Hankuk University of Foreign Studies   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030599275     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01554-7     Document Type: Article

References (21)

1. 1. This paper is part 5 in the series of "Lewis acid induced N-methyleneamine equivalents". For part 4 see, H.-J. Ha, K.-H. Kang, Y.-G. Ann and S.-J. Oh, submitted to J. Chem. Soc. Perkin Trans. I.
2. 2. For a comprehensive review see, Tanner, D. Angew, Chem. Int. Ed. Engl. 1994, 33, 599.
3. 3. (a) Satoh, T; Sato, T.; Oohara, T.; Yamakawa, K. J. Org Chem. 1989, 54, 3973.
4. (b) Cainelli, G.; Panunzio, M.; Giacomini, D. Tetrahedron Lett. 1991, 32, 121.
5. (c) Lim, Y.; Lee, W, K. Tetrahedron Lett. 1995, 36, 8431.
6. (d) Baldwin, J. E.; Farthing, C. N.; Russell, A. T.; Schofield, C. J.; Spivey, A. C. Tetrahedron Lett. 1996, 37, 3761.
7. 4. (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
8. (b) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742.
9. (c) Aires-de-Sousa, J.; Lobo, A. M.; Prabhakar, S. Tetrahedron Lett. 1996, 37, 3183.
10. (d) Carducci. M.; Fioravanti, S.; Loreto, M. A.; Pellacani, L.; Tardella, P. A. Tetrahedron Lett. 1996, 37, 3777.
11. 5. (a) Hansen, K. B.; Finney, N. S.; Jacobsen, E. N. Angew. Chem. Int. Ed. Engl. 1995, 34, 676.
12. (b) Rasmussen, K. G.; Jorgensen, K. A. J. Chem, Soc. Chem. Commun., 1995, 1401.
13. 6. (a) Ha, H.-J.; Nam, G.-S.; Park, K. P. Bull. Kor. Chem. Soc. 1990, 11, 485.
14. (b) Ha, H.-J.; Nam, G.-S.; Park, K. P. Tetrahedron Lett, 1990, 31, 1567.
15. (c) Ha, H.-J.; Nam, G.-S.; Park, K. P. Synth. Commun. 1991, 21, 155.
16. (d) Ha, H.-J. ; Ahn, Y.-G. Synth. Commun. 1995, 25, 969.
17. (e) Ha, H.-J. ; Ahn, Y.-G.; Chon, J.-K. J. Chem. Soc. Perkin Trans. I, 1995, 2631.
18. 4, filtered, and concentrated under reduced pressure. The crude reaction product was purified by flash chromatography to give aziridine-2-carboxylates.
19. 4 at -15°C.
20. 1H NMR. See reference, 3(c).
21. 2 in relatively lower reaction yields.