1610
E. P. Pec¸anha et al. / Tetrahedron Letters 43 (2002) 1607–1611
9. (a) Tius, M. A.; Bush-Petersen, J. Tetrahedron Lett. 1994,
56, 4289–5295; (b) Imagawa, H.; Shigaraki, T.; Suzuki,
T.; Takao, H.; Yamada, H.; Sugihara, T.; Nishizawa, M.
Chem. Pharm. Bull. 1998, 46, 1341–1342.
10. Garavelas, A.; Mavropoulos, I.; Perlmutter, P.; West-
man, G. Tetrahedron Lett. 1995, 36, 463–466.
11. Purchased from Aldrich Co., Milwaukee, USA.
12. Derivative synthesized in 71% yield from Dieckmann
cyclization of ethyl adipate, using AlCl3/Et3N in CH2Cl2.
For a detailed description, see: Pec¸anha, E. P.; Barreiro,
E. J.; Fraga, C. A. M. Quimica Nova 1997, 20, 435–437.
13. Barco, A.; Benetti, S.; Pollini, G. P. Synthesis 1973, 316.
14. (a) Fraga, C. A. M.; Barreiro, E. J. Synth. Commun.
1995, 25, 1133–1144; (b) Teixeira, L. H. P.; Barreiro, E.
J.; Fraga, C. A. M. Synth. Commun. 1997, 27, 3241–3257.
15. Banwell, M. G.; Bui, C. T.; Pham, H. T. T.; Simpson, G.
W. J. Chem. Soc., Perkin Trans. 1 1996, 967–969.
16. Menezes, C. M. S.; Teixeira, L. H. P.; Sant’ Anna, C. M.
R.; Rodrigues, C. R.; Barreiro, E. J.; Fraga, C. A. M.
2001, unpublished results. These data were obtained from
molecular modeling studies, using semiempirical PM3
method.
Figure 4. Simulation of time dependent solvation of the com-
pound (7b): (a) distance between terminal methyl group and
carbonyl oxygen; (b) dihedral angle (q) analyses.
Acknowledgements
Thanks are due to CNPq (BR., grants c50.0033/96-5,
c460200/00-3 and fellowships), FAPERJ (BR.) and
FUJB (BR.) for financial support. We are grateful to
Analytical Center of NPPN (UFRJ-BR.) for spectro-
scopic facilities. We are indebted to Professor Carlos
M. R. Sant’Anna (UFRRJ–BR.) for molecular model-
ing suggestions.
17. Roubaud, V.; Le Moigne, F.; Mercier, A.; Tordo, P.
Synth. Commun. 1996, 26, 1507–1516.
18. The 2-azabicyclo[3.3.0]octane derivatives (5a) and (5b)
were obtained as a mixture of free secondary amines and
NH–BH3 complexes. This mixture were converted into
desired free secondary amines after acidic treatment.
19. 1H and 13C NMR spectra were determined in CDCl3/
TMS, with UNITY plus-300 at 300 and 75 MHz,
respectively.
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we set the parameter NPPA to 1082 and NSPA to 42.
The effective VDW radius of the solvent molecule was
,
2.69 A. All structures were optimized to a gradient norm
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<0.1 in the gas phase and <0.6 in the solvent phase, using
the eigenvector method (EF) at PRECISE level. Parallel
to these methods a molecular dynamics simulation of (7)