Stereoselective Synthesis of 2β-Carbomethoxy-3β-phenyltropane Derivatives. Enhanced Stereoselectivity Observed for the Conjugate Addition Reaction of Phenylmagnesium Bromide Derivatives with Anhydro Dichloromethane

Journal of Heterocyclic Chemistry

Volumn 33, Issue 6, 1996, Pages 2037-2039

  Xu, Lifen ^a   Trudell, Mark L ^a  

^a UNIVERSITY OF NEW ORLEANS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TROPANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030483653     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570330676     Document Type: Article

References (19)

1. R. L. Clarke, S. J. Daum, A. J. Gambino, M. D. Aceto, J. Pearl, M. Levitt, W. R. Cumiskey, and E. F. Bogado, J. Med. Chem., 16, 1260 (1973).
2. R. A. Milius, J. K. Saha, B. K. Madras, and J. L. Neumeyer, J. Med. Chem., 34, 1728 (1991).
3. F. I. Carroll, Y. Gao, M. A. Rahman, P. Abraham, K. Parham, A. H. Lewin, J. W. Boja and M. J. Kuhar, J. Med. Chem., 34, 2719 (1991).
4. F. I. Carroll, A. H. Lewin, J. W. Boja, and M. J. Kuhar, J. Med. Chem., 35, 969 (1992).
5. P. C. Meltzer, A. Y. Liang, A.-L. Brownell, D. R. Elmaleh, and B. K. Madras, J. Med. Chem., 36, 855 (1993).
6. A. P. Kozikowski, M. K. E. Saiah, K. M. Johnson, and J. S. Bergmann, J. Med. Chem., 38, 3086 (1995).
7. S. V. Kelkar, S. Izenwasser, J. L. Katz, C. L. Klein, N. Zhu, and M. L. Trudell, J. Med Chem., 37, 3875 (1994).
8. E. C. Ashby, J. Laemmle, and H. M. Neumann, Acc. Chem. Res., 7, 277 (1974).
9. H. W. H. J. Bodewitz, C. Blomberg, and F. Bickelhaupt, Tetrahedron, 31, 1053 (1975).
10. E. C. Ashby and T. L. Wiesemann, J. Am. Chem. Soc., 100, 189 (1978).
11. C. Cianetti, G. DiMaio, V. Pignatelli, P. Tagliatesta, E Vecchi, and E. Zeuli Tetrahedron, 39, 657 (1983).
12. B. Miller, E. R. Matjeka, and J. G. Haggerty, J. Org. Chem., 49, 3121 (1984).
13. W. Schmid and G. M. Whitesides, J. Am. Chem. Soc., 112, 9670 (1990).
14. D. J. Cram and F. A. Abd Elhafetz, J. Am. Chem. Soc., 74, 5828 (1952).
15. E. L. Eliel in Asymmetric Synthesis, Vol 2, J. D. Morrison, ed, Academic Press, New York, 1983, p 125.
16. B. Reitstoyen, L. Kilaas, and T. Anthonsen, Acta Chem. Scand., B40, 440 (1986).
17. H. G. Viehe and M. Reinstein, Chem. Ber., 95, 2557 (1962).
18. D. J. Nelson, R. DiFrancesco, and D. Petters, J. Chem. Educ., 54, 648 (1977).
19. Available from NIDA Drug Supply System, Research Technology Branch.