Aldol condensation reactions of tricarbonyliron complexes. Easy access to diastereomerically pure 1,2,3 trisubstituted 1,3 diols from α-substituted dienone complexes

Tetrahedron Letters

Volumn 41, Issue 21, 2000, Pages 4213-4217

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

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

IRON COMPLEX; KETONE DERIVATIVE; TRICARBOXYLIC ACID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; DIASTEREOISOMER; POLYMERIZATION; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034729457     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00568-2     Document Type: Article

References (12)

1. Franck-Neumann, M.; Colson, P. J.; Geoffroy, P.; Taba, K. M. Tetrahedron Lett. 1992, 33, 1903; Franck-Neumann, M.; Bissinger, P.; Geoffroy, P. Tetrahedron Lett. 1997, 38, 4477, and references cited therein.
2. Franck-Neumann, M.; Colson, P. J.; Geoffroy, P.; Taba, K. M. Tetrahedron Lett. 1992, 33, 1903; Franck-Neumann, M.; Bissinger, P.; Geoffroy, P. Tetrahedron Lett. 1997, 38, 4477, and references cited therein.
3. Clinton, N. A.; Lillya, C. P. J. Am. Chem. Soc. 1970, 92, 3058.
4. Narasaka, K.; Pai, F. C. Tetrahedron 1984, 40, 2233.
5. Macrolide Antibiotics; Omura, S., Ed.; Academic Press, 1984. Boeckman, R. K.; Goldstein Jr., S. W. The Total Synthesis of Natural Products; Apsimon, J., Ed. The total synthesis of macrocyclic lactones. John Wiley & Sons, 1988; Vol. 7, pp. 1-139.
6. Macrolide Antibiotics; Omura, S., Ed.; Academic Press, 1984. Boeckman, R. K.; Goldstein Jr., S. W. The Total Synthesis of Natural Products; Apsimon, J., Ed. The total synthesis of macrocyclic lactones. John Wiley & Sons, 1988; Vol. 7, pp. 1-139.
7. Macrolide Antibiotics; Omura, S., Ed.; Academic Press, 1984. Boeckman, R. K.; Goldstein Jr., S. W. The Total Synthesis of Natural Products; Apsimon, J., Ed. The total synthesis of macrocyclic lactones. John Wiley & Sons, 1988; Vol. 7, pp. 1-139.
8. The preparation of the complexes 1a, 1b, 1d and 1e has been described: Franck-Neumann, M.; Chemla, P.; Martina, D. Synlett 1990, 641; Franck-Neumann, M.; Geoffroy, P.; Winling, A. Tetrahedron Lett. 1995, 36, 8213. More convenient preparations of 1a-e, even in the optically active series, have since been achieved (Bissinger, P. PhD, Université Louis Pasteur de Strasbourg, 1996) and will be published in a forthcoming detailed paper: Franck-Neumann, M.; Bissinger, P.; Geoffroy, P. Tetrahedron: Asymmetry).
9. The preparation of the complexes 1a, 1b, 1d and 1e has been described: Franck-Neumann, M.; Chemla, P.; Martina, D. Synlett 1990, 641; Franck-Neumann, M.; Geoffroy, P.; Winling, A. Tetrahedron Lett. 1995, 36, 8213. More convenient preparations of 1a-e, even in the optically active series, have since been achieved (Bissinger, P. PhD, Université Louis Pasteur de Strasbourg, 1996) and will be published in a forthcoming detailed paper: Franck-Neumann, M.; Bissinger, P.; Geoffroy, P. Tetrahedron: Asymmetry).
10. The preparation of the complexes 1a, 1b, 1d and 1e has been described: Franck-Neumann, M.; Chemla, P.; Martina, D. Synlett 1990, 641; Franck-Neumann, M.; Geoffroy, P.; Winling, A. Tetrahedron Lett. 1995, 36, 8213. More convenient preparations of 1a-e, even in the optically active series, have since been achieved (Bissinger, P. PhD, Université Louis Pasteur de Strasbourg, 1996) and will be published in a forthcoming detailed paper: Franck-Neumann, M.; Bissinger, P.; Geoffroy, P. Tetrahedron: Asymmetry).
11. Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511.
12. Franck-Neumann, M.; Geoffroy, P.; Gumery, F. Tetrahedron Lett. 2000, 41, 4219-4222.