Diastereoselective synthesis of trisubstituted cyclopentane- and cyclohexanecarboxylic acid derivatives mediated by iron tricarbonyl

Journal of Organic Chemistry

Volumn 61, Issue 11, 1996, Pages 3874-3877

  Yeh, Ming Chang P ^a   Chuang, L W ^a   Ueng, C H ^a  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000927231     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952148k     Document Type: Article

References (15)

1. For five-membered ring see: (a) Trost, B. M.; Romero, D. L.; Rise, F. J. Am. Chem. Soc. 1994, 116, 4268.
2. (b) Taber, D. F.; You, K. K. J. Am. Chem. Soc. 1995, 117, 5757.
3. (c) Ramaiah, M. Synthesis, 1984, 529.
4. (d) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer: New York, 1987.
5. (e) Trost, B. M. Chem. Soc. Rev. 1982, 11, 141.
6. (f) Pauson, P. L.; Khand, I. U. Ann. N. Y. Acad. Sci. 1977, 295, 2.
7. For six-membered ring see: (a) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415. (b) Stork, G.; Chan, T. Y.; Breault, G. A. J. Am. Chem. Soc. 1992, 114, 7578.
8. For six-membered ring see: (a) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415. (b) Stork, G.; Chan, T. Y.; Breault, G. A. J. Am. Chem. Soc. 1992, 114, 7578.
9. Yeh, M. C. P.; Sheu, B. A.; Fu, H. W.; Tau, S. I.; Chuang, L. W. J. Am. Chem. Soc. 1993, 115, 5941.
10. A coupling constant of 8.0-Hz for cis protons in the five-membered ring is reported with a dihedral angle of 43°. Trost, B. M.; Romero, D. L.; Rise, F. J. Am. Chem. Soc. 1995, 116, 4268.
11. The generation of carboxylic acid derivatives via oxidation of iron-carbon bonds is also proposed for alkylation and bromination of the tetracarbonyliron dianion (known as the Collman reagent). Collman, J. P. Acc. Chem. Res. 1975, 8, 342.
12. Majid, T. H.; Yeh, M. C. P.; Knochel, P. Tetrahedron Lett. 1989, 30, 5069.
13. Coupling constants of 8.4, 8.0 Hz were observed for a cis, cis trisubstituted cycloheptane. See: Lautens, M.; Kumanovic, S. J. Am. Chem. Soc. 1995, 117, 1954.
14. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
15. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.