Aldol condensation reactions of (Dienone) tricarbonyliron complexes. 3. Enantioselective total synthesis of 3,6-Dideoxyhexoses from lactaldehyde

Tetrahedron Letters

Volumn 38, Issue 25, 1997, Pages 4473-4476

  Franck Neumann, Michel ^a   Bissinger, Paul ^a   Geoffroy, Philippe ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

LACTALDEHYDE; MONOSACCHARIDE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030950923     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00905-2     Document Type: Article

References (12)

1. Proceeding communication : Franck-Neumann, M.; Bissinger, P.; Geoffroy, P. Tetrahedron Lett.....
2. Franck-Neumann, M.; P. Chemla, P.; Martina, D. Synlett, 1990, 641.
3. Westphal, O.; Lüderitz, O Angew. Chem., 1960, 23, 881.
4. Ito, Y.; Kobayashi, Y.; Kawabata, T.; Takase, M.; Terashima, S. Tetrahedron, 1989, 45, 5767.
5. Reetz, M.T.; Raguse, B.; Marth, C.F.; Hügel, H.M.; Bach, T.; Fox, D.N.A. Tetrahedron, 1992, 48, 5731 and ref. therein.
6. Franck-Neumann, M., Colson, P.J.; Geoffroy, P.; Taba, K.M. Tetrahedron Lett., 1992, 33, 1903.
7. 3, 100 MHz, ppm/TMS) : (-)-9 : δ = 14.9, 19.1, 19.5, 29.8, 34.5, 57.0, 65.1, 70.7, 71.7, 71.8, 76.7, 80.1, 85.4, 98.8, 127.4, 127.7, 128.3, 139.1 ; (-)-11 : δ = 15.3, 19.1, 24.2, 25.0, 37.0, 57.0, 65.7, 65.8, 68.2, 69.9, 71.7, 79.9, 85.0, 100.6, 127.4, 127.7, 128.3, 139.0.
8. Rychnovsky, S.D., Rogers, B., Yang, G. J. Org. Chem., 1993, 58, 3511.
9. Nicolaou, K.C.; Magolda, R.L. J. Org. Chem., 1981, 46, 1506.
10. No contamination of (+)-16 by (-)-17 or vice versa was observed : the decomplexation and ozonolysis steps proceeded therefore without any epimerization.
11. 12 and the racemic complex 1 one would also obtain the ketols (-)-4 and (+)-6.
12. Feenstra, R.W.; Stokkingreef, E.H.M.; Nivard, R.J.F.; Ottenheijm, H.C.J. Tetrahedron, 1988, 44, 5583.