A short synthesis of chiral peraza-macrocycles through opening of cyclic sulfamidates

Tetrahedron Letters

Volumn 40, Issue 43, 1999, Pages 7687-7690

  Kim, B Moon ^a   So, Soon Mog ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BENZYLAMINE DERIVATIVE; ESTER DERIVATIVE; MACROCYCLIC COMPOUND; SULFAMIDE DERIVATIVE;

ARTICLE; CHIRALITY; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0033595872     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01545-2     Document Type: Article

References (27)

1. (a) Bradshaw, J. S.; Krakowiak, K. E.; Izatt, R. M. Aza-Crown Macrocycles; John Wiley & Sons: New York, 1993;
2. (b) Parker, D. In Macrocycle Synthesis; Parker, D., Ed.; Oxford University Press: Oxford, 1996.
3. Pederson, C. J. J. Am. Chem. Soc. 1967, 89, 7017.
4. (a) Murakami, Y.; Kikuchi, J.-i.; Hisaeda, Y.; Hayashida, O. Chem. Rev. 1996, 96, 721.
5. (b) Koike, T.; Watanabe, T.; Aoki, S.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1996, 118, 12696.
6. (c) Kimura, E.; Hashimoto, H.; Koike, T. J. Am. Chem. Soc. 1996, 118, 10963.
7. (d) Kimura, E.; Kitamura, H.; Koike, T.; Shiro, M. J. Am. Chem. Soc. 1997, 1198, 10909.
8. (e) Aoki, S.; Honda, Y.; Kimura, E. J. Am. Chem. Soc. 1998, 120, 10018.
9. (f) Jang, B. B.; Lee, K. P.; Min, D. H.; Suh, J. H J. Am. Chem. Soc. 1998, 120, 12008.
10. (g) You, J. S.; Yu, X. Q.; Li, X. S.; Yan, Q. S.; Xie, R. G. Tetrahedron: Asymmetry 1998, 9, 1197.
11. (a) Ranganathan, D.; Haridas, V.; Madhusudanan, K. P.; Roy, R.; Nagaraj, R.; John, G. B. J. Am. Chem. Soc. 1997, 119, 11578.
12. (b) Alfonso, I.; Rebolledo, F.; Gotor, V. Tetrahedron: Asymmetry 1999, 10, 367.
13. (c) Tripier, R.; Siri, O.; Rabiet, F.; Denat, F.; Guilard, R. Tetrahedron Lett. 1999, 40, 79.
14. (d) Choi, H. J.; Kwak, M. O.; Kim, J. M. Tetrahedron Lett. 1997, 38, 6217.
15. (e) Grossel, M. C.; Hamilton, D. G.; Vine, T. A. Tetrahedron Lett. 1997, 38, 4639.
16. (f) Joly, J. P.; Schroder, G. Tetrahedron Lett. 1997, 38, 8197.
17. (g) Habata, Y.; Bradshaw, J. S.; Zhang, X. X.; Izatt, R. M. J. Am. Chem. Soc. 1997, 119. 7145.
18. (h) Kim, B. H.; Jeong, E. J.; Jung, W. H. J. Am. Chem. Soc. 1995, 117, 6390.
19. (i) Hellier, P. C.; Bradshaw, J. S.; Young, J. J.; Zhang, X. X.; Izatt, R. M. J. Org. Chem. 1996, 61, 7270.
20. (j) Gryko, D. T.; Piatet, P.; Salanaki, P.; Jurczak, J. Tetrahedron: Asymmetry 1998, 9, 1771.
21. Kim, B. M.; So, S. M. Tetrahedron Lett. 1998, 39, 5381.
22. +; found: 520.2810.
23. +; found: 1091.5847.
24. Richman, J. E.; Atkins, T. J. J. Am. Chem. Soc. 1974, 96, 2268.
25. +; found: 560.3130.
26. For the preservation of stereochemical integrity at the α-center under the reaction conditions involving cyclic sulfamidates of serine ester derivatives, see Ref. 5.
27. These include Vydac 218TP54 (4.6×250 mm), Phenomenex Chirex 00G-3005-E0 (4.6×250 mm), and Daicel Chiralcel OD-R (4.6×250 mm) columns for reverse phase analyses and Phenomenex Chirex 00G-3014-E0 (4.6×250 mm) and Daicel Chiralcel OD (4.6×250 mm) columns for normal phase ones.