Synthesis of chiral ferrocenyl aminoalcohols involving a diastereospecific oxidation: Use in asymmetric catalysis

Tetrahedron Asymmetry

Volumn 10, Issue 22, 1999, Pages 4417-4425

  Delacroix, Olivier ^a   Picart Goetgheluck, Sophie ^a   Maciejewski, Lucien ^a   Brocard, Jacques ^a  

^a UNITÉ DE CATALYSE ET DE CHIMIE DU SOLIDE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHIRALITY; OXIDATION; PRIORITY JOURNAL; STEREOISOMERISM; SYNTHESIS;

EID: 0033388688     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00495-4     Document Type: Article

References (24)

1. Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1986-2012.
2. (a) Stewart, J.; Reed, K.; Kayser, M. J. Chem. Soc., Perkin Trans. 1 1996, 755-757.
3. (b) Alphand, V.; Furstoss, R.; Pedragosa-Moreau, S.; Roberts, S.; Willetts, A. J. Chem. Soc., Perkin Trans. 1 1996, 1867-1872.
4. (a) Zhao, S.; Samuel, O.; Kagan, H. Tetrahedron 1987, 43, 21, 5135-5144.
5. (b) Adam, W.; Korb, M.; Roschmann, K.; Saha-Moller, C. J. Org. Chem. 1998, 63, 3423-3428.
6. (c) Palombi, L.; Bonadies, F.; Pazienza, A.; Scettri, A. Tetrahedron: Asymmetry 1998, 9, 1817-1822.
7. (a) Burns, C.; Martin, C.; Sharpless, K. J. Org. Chem. 1989, 54, 2826-2834.
8. (b) Kitano, Y.; Matsumoto, T.; Sato, F. Tetrahedron 1988, 44, 13, 4073-4086.
9. (c) Zhang, W.; Jacobsen, E. J. Org. Chem 1991, 56, 2296-2298.
10. (d) Jacobsen, E.; Zhang, W.; Muci, A.; Ecker, J.; Deng, L. J. Am. Chem. Soc 1991, 113, 7063-7064.
11. Hashiguchi, S.; Fuji, A.; Haack, K.-J.; Matsumura, K.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 288-290.
12. Mijs, W. J.; De Jonge, C. R. H. I. Organic Syntheses by Oxidation with Metal Compounds; Plenum Press: New York, 1986; pp. 132-134 and 243.
13. (a) Maciejewski, L.; Goetgheluck, S.; Delacroix, O.; Brocard, J. Tetrahedron: Asymmetry 1996, 7, 1573-1576.
14. (b) Pasquier, C.; Naili, S.; Pélinski, L.; Brocard, J.; Mortreux, A.; Agbossou, F. Tetrahedron: Asymmetry 1998, 9, 193-196.
15. (c) Bastin, S.; Delebecque, N.; Brocard, J.; Pélinski, L. Tetrahedron: Asymmetry 1996, 10, 1647-1651.
16. Delacroix, O.; Picart-Goetgheluck, S.; Maciejewski, L.; Brocard, J. Tetrahedron: Asymmetry 1999, 10, 1835-1837.
17. Nicolosi, G.; Patti, A.; Morrone, R.; Piattelli, M. Tetrahedron: Asymmetry 1994, 5, 1275-1280.
18. (a) All the metallocene chiralities were determined according to the nomenclature of Cahn, Ingold and Prelog extended to planar chiralities by Schlögl: Schlögl, K. Topics in Stereochemistry 1967, 1, 39-91. (b) The denomination 1′R or 1′S refers to planar chirality; the 1R or 1S one refers to central chirality.
19. (a) All the metallocene chiralities were determined according to the nomenclature of Cahn, Ingold and Prelog extended to planar chiralities by Schlögl: Schlögl, K. Topics in Stereochemistry 1967, 1, 39-91. (b) The denomination 1′R or 1′S refers to planar chirality; the 1R or 1S one refers to central chirality.
20. The relative configurations of the major diastereomer of 2, 3 and 4 were determined according to Bau's studies: Battelle, L. F.; Bau, R.; Gokel, G. W.; Oyakawa, R. T.; Ugi, I. K. J. Am. Chem. Soc. 1973, 95, 482-486.
21. (a) Noyori, R.; Kitamura, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 49-69.
22. (b) Soaï, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856.
23. Soaï, K.; Ookawa, A.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc. 1987, 109, 7111.
24. (b) Mukaiyama, T.; Hojo, K. Chem. Lett. 1976, 893.