De novo synthesis of sugar-aza-crown ethers via a domino Staudinger aza-Wittig reaction

Journal of Organic Chemistry

Volumn 71, Issue 8, 2006, Pages 3295-3298

  Ménand, Mickaël ^a   Blais, Jean Claude ^a   Valéry, Jean Marc ^a   Xie, Juan ^b  

^a Centre National de la Recherche Scientifique   (France)

^b Ecole Normale Superieure de Cachan   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; DIMERIZATION; DIMERS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CYCLODIMERIZATION; SUGAR-AZA-CROWN (SAC) ETHERS; WITTIG REACTION;

ETHERS;

CROWN ETHER DERIVATIVE; HETEROCYCLIC COMPOUND;

ARTICLE; COMPLEX FORMATION; DIMERIZATION; HORNER REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 33645776896     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052489q     Document Type: Article

References (24)

1. Gokel, G. W.; Leevy, W. M.; Weber, M. E. Chem. Rev. 2004, 104, 2723-2750.
2. Bünzli, J.-C. G.; Piguet, C. Chem. Soc. Rev. 2005, 34, 1048-1077.
3. (a) Faltin, F.; Fehring, V.; Miethchen, R. Synthesis 2002, 1851-1856 and references therein.
4. (b) Bakó, T.; Bakó, P.; Keglevich, G.; Bombicz, P.; Kubinyi, M.; Pál, K.; Bodor, S.; Makó, A.; Tóke, L. Tetrahedron: Asymmetry 2004, 15, 1589-1595.
5. Ménand, M.; Blais, J.-C.; Hamon, L.; Valéry, J.-M.; Xie, J. J. Org. Chem. 2005, 70, 4423-4430.
6. (a) Fürstner, A.; Albert, M.; Mlynarski, J.; Matheu, M.; DeClercq, E. J. Am. Chem. Soc. 2003, 125, 13132-13142.
7. (b) Takahashi, S.; Souma, K.; Hashimoto, R.; Koshino, H.; Nakata, T. J. Org. Chem. 2004, 69, 4509-4515.
8. (a) Korupoju, S. R.; Zacharias, P. S. Chem. Commun. 1998, 1267-1268.
9. (b) Bru, M.; Alfonso, I.; Isabel Burguete, M.; Luis, S. V. Tetrahedron Lett. 2005, 46, 7781-7785.
10. Chong, P. Y.; Petillo, P. A. Org. Lett. 2000, 2, 1093-1096.
11. (a) Chakraborty, T. K.; Srinivasu, P.; Bikshapathy, E.; Nagaraj, R.; Vairamani, M.; Kiran Kumar, S.; Kunwar, A. C. J. Org. Chem. 2003, 68, 6257-6263.
12. (b) Azumaya, I.; Okamoto, T.; Imabeppu, F.; Takayanagi, H. Heterocycles 2003, 60, 1419-1424.
13. (c) Mayes, B. A.; Cowley, A. R.; Ansell, C. W. G.; Fleet, G. W. J. Tetrahedron Lett. 2004, 45, 163-166.
14. (d) Haberhauer, G. Synlett 2004, 1003-1006.
15. (e) Chakraborty, T. K.; Tapadar, S.; Venugopal Raju, T.; Annapurna, J.; Singh, H. Synlett 2004, 2484-2488.
16. (a) Bodine, K. D.; Gin, D. Y.; Gin, M. S. J. Am. Chem. Soc. 2004, 126, 1638-1639.
17. (b) Bodine, K. D.; Gin, D. Y.; Gin, M. S. Org. Lett. 2005, 7, 4479-4482.
18. (a) Gololobov, Y. G.; Zhmurova, I. N.; Kasukhin, L. F. Tetrahedron 1981, 37, 437-472.
19. (b) Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188-5240.
20. Xie, J.; Ménand, M.; Valéry, J.-M. Carhohydr. Res. 2005, 340, 481-487.
21. Xie, J. Eur. J. Org. Chem. 2002, 3411-3418.
22. Yu, W.; Mei, Y.; Kang, Y.; Hua, Z.; Jin, Z. Org. Lett. 2004, 6, 3217-3219.
23. Couturier, M.; Tucker, J. L.; Andresen, B. M.; Dubé, P.; Negri, J. T. Org. Lett. 2001, 3, 465-467.
24. Shao, H.; Wang, Z.; Lacroix, E.; Wu, S.-H.; Jennings, H. J.; Zou, W. J. Am. Chem. Soc. 2002, 124, 2130-2131.