Inversion at the bridgehead nitrogen of the 1-azabicyclo[4.4.0]decane ring system

Tetrahedron Letters

Volumn 40, Issue 20, 1999, Pages 3851-3854

  Slough, Greg A ^a   Fusen, Han ^b   Lee, Byung H ^b  

^a KALAMAZOO COLLEGE   (United States)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 AZABICYCLO[4.4.0]DECANE; DECANE; NITROGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; LOW TEMPERATURE PROCEDURES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 0033553501     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00641-3     Document Type: Article

References (10)

1. 1. For a recent review of amine stereodynamics, see: Bushweller, C.H. Acyclic Organonitrogen Stereodynamics; Lambert, J. B.; Takeuchi, Y., Eds.; VCH Publishers: New York, 1992.
2. 2. Forsyth, D. A.; Zhang, W.; Hanley, J. A. J. Org. Chem. 1996, 61, 1284 and references therein.
3. 3. Latvala, A.; Onur, M. A.; Gozler, T.; Linden, A.; Kivcak, B.; Hesse M. Tetrahedron Asymmetry 1995, 6, 361.
4. 4. Davies, J. W.; Malpass, J. R.; Fawcett, J.; Prouse, L. J. S.; Lindsay, R.; Russell, D. R. J. Chem. Soc., Chem. Commun. 1986, 1135.
5. 5. Bushweller, C. H.; Brown, J. H.; DiMeglio, C. M.; Gribble, G. W.; Eaton, J. T.; LeHoullier, C. S.; Olson, E. R. J. Org. Chem. 1995, 60, 268 and references therein.
6. 2 are statistically about twice as large as those based on F, and R-factors based on all data will be even larger. In the final refinement, with 2,173 reflections have intensities > 4s:R = 0.066; S = 3.42. R = 0.080 with all 3,002 reflections. The two molecules in the asymmetrical unit have different conformations.
7. 7. Polonsky, J; Merrien, M. A.; Prange, T.; Pascard, C.; Moreau, S. J. Chem. Soc., Chem. Commun. 1980, 601.
8. 8. Lee, B. H.; Clothier, M. F. J. Org. Chem. 1997, 62, 1863.
9. 9. The original X-ray coordinates were transferred to our proprietary computer modeling system, Mozaic®, and the two invertomers modeled side by side.
10. 10. To verify the assignment of decoalesed proton signals on C17 at 203 K a correlated spectrum (COSY) was obtained. Both signals at 2.44 and 2.31 ppm showed separate cross peaks at 2.62 ppm. A single cross peak at the resonance frequency was observed in the 293 K COSY.