Synthesis and conformational analysis of 2,6-dimethyl-1,5-diaza-cis-decalins

Tetrahedron

Volumn 57, Issue 21, 2001, Pages 4537-4542

  Kozlowski, Marisa C ^a   Xu, Zhenrong ^a   Santos, A Gil ^b  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b UNIVERSIDADE NOVA DE LISBOA   (Portugal)

Author keywords

Chiral diamine; Conformational switch; Diazadecalin

Indexed keywords

2,6 DIMETHYL 1,5 DIAZADECALIN DERIVATIVE; DECALIN DERIVATIVE; METHYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL MODIFICATION; CIS ISOMER; CONFORMATION; ISOMERISM; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0035927234     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)00370-2     Document Type: Article

References (17)

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3. Li, X.; Yang, J.; Kozlowski, M. C. Org. Lett. 2001, 3 (in press).
4. This goal cannot be accomplished by simple substitution at nitrogen since N- or N,N′-substitution favors the N-out conformation. See Refs. 1 and 5.
5. Ganguly B., Freed D.A., Kozlowski M.C. J. Org. Chem. 66:2001;1103-1108.
6. Beak P., Lee W.K.J. Org. Chem. 55:1990;2578-2580.
7. Gawley R.E., Zhang Q. Tetrahedron. 50:1994;6077-6088.
8. 1,3 strain between the Boc and the equatorial Me upon chair-chair interconversion.
9. In a further example, metalation-alkylation of Boc-cis-decahydroquinoline, which is isosteric to 3, by Meyers et al. also resulted in trans-substituted piperdine ring. See: Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652-6660.
10. Under these conditions a mixture of conformers was generally observed with 3-out predominating. This mixture was used directly in the next step.
11. Tanaka K., Yoshifuji S., Nitta Y. Chem. Pharm. Bull. 36:1988;3125-3129.
12. Herdeis C., Heller E. Tetrahedron: Asymmetry. 4:1993;2085-2094.
13. The calculated NMR coupling constants and the relative energies in Fig. 1 were determined using MacroModel 6.0. (a) MacroModel ver. 6.0; Still, W. C., Columbia Univ. (b) Mohamdi F., Richards N.G., Guida W.C., Liskamp R., Lipton M., Caufield C., Chang G., Hendrickson T., Still W.C. J. Comput. Chem. 11:1990;440-467.
14. The experimental NMR coupling constants in Table 1 were determined by spectral reproduction using gNMR v3.6 © IvorySoft 1992-1996 from Cherwell Scientific Publishing; Oxford, UK.
15. 2)=9.86%, GOF=1.089 for 224 parameters and 2076 unique reflections with I>2σ(I).
16. Equatorial substitution appears more important than other effects. See Ref. 5.
17. Dollinger L.M., Ndakala A.J., Hashemzadeh M., Wang G., Wang Y., Martinez I., Arcari J.T., Galluzzo D.J., Howell A.R., Rheingold A.L., Figuero J.S.J. Org. Chem. 64:1999;7074-7080.