Highly stereoselective synthesis of 3-amino-3,6-dideoxyaldohexoses by tin triflate mediated aldol condensation reaction of tricarbonyl iron α- aminodienone complexes. Total synthesis of multiprotected mycosamine

Tetrahedron Letters

Volumn 40, Issue 14, 1999, Pages 2829-2832

  Franck Neumann, Michel ^a   Miesch Gross, Laurence ^b   Gateau, Christelle ^b  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

HEXOSE;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; ORGANIC CHEMISTRY; POLYMERIZATION;

EID: 0033515714     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00271-3     Document Type: Article

References (21)

1. Walters, D.R.; Dutcher, J.D.; Wintersteiner, O. J. Am. Chem. Soc. 1957, 79, 5076.
2. Von Saltza, M.H.; Reid, J.; Dutcher, J.D.; Wintersteiner O. J. Am. Chem. Soc. 1961, 83, 2785.
3. Nicolaou, K.C.; Daines, R.A.; Chakraborty, T.K.; Ogawa, Y. J. Am. Chem. Soc. 1987, 109, 2821.
4. Franck-Neumann, M.; Abdali, A.; Colson, P.J.; Sedrati, M. Synlett 1991, 331.
5. 16 failed.
6. Staudinger, H.; Hauser, E. Helv. Chim. Acta 1920, 3, 861.
7. Knouzi, N.; Vaultier, M.; Carrié, R. Bull. Soc. Chim. Fr. 1985, 815.
8. An analogous reaction has been observed by Borowitz and coworkers on secondary and tertiary α-bromoketones with triphenylphosphine. Borowitz, I.J.; Grossman, L.I. Tetrahedron Lett. 1962, 471.
9. Saito, S.; Nakajima, H.; Inaba, M.; Moriwake, T. Tetrahedron Lett. 1989, 30, 837.
10. Franck-Neumann, M.; Bissinger, P.; Geoffroy, P. Tetrahedron Lett. 1997, 38, 4473.
11. Mukaiyama, T.; Iwasawa, N.; Stevens, R.W.; Haga, T. Tetrahedron 1984, 40, 1381.
12. Mukaiyama, T.; Stevens, R.W.; Iwasawa, N. Chem. Lett. 1982, 353.
13. 2O 3:1).
14. 3).
15. Clinton, N.A.; Lillya, C.P. J. Am. Chem. Soc. 1970, 92, 3058.
16. Evans, D.A.; Chapman, K.T. Tetrahedron Lett. 1986, 27, 5939.
17. (Formula presented)
18. Ito, Y.; Kobayashi, Y.; Kawabata, T.; Takase, M.; Terashima, S. Tetrahedron 1989, 45, 5767.
19. Flitsch, W.; Hohenhorst, M. Liebigs Ann. Chem. 1990, 397.
20. Franck-Neumann, M.; Chemla, P.; Martina, D. Synlett 1990, 641.
21. Franck-Neumann, M.; Bissinger, P.; Geoffroy, P. Tetrahedron Lett. 1997, 38, 4469.