Trifluoromethyl-substituted Δ3-imidazolines: Synthesis and reactivity

Tetrahedron Letters

Volumn 38, Issue 25, 1997, Pages 4359-4362

  Derstine, Christopher W ^a   Smith, David N ^a   Katzenellenbogen, John A ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLINE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030939349     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00934-9     Document Type: Article

References (10)

1. Derstine, C. W.; Smith, D. N.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1996, 118, 8485.
2. Achiwa, K.; Sekiya, M. Chem. Lett. 1981, 1213.
3. Achiwa, K.; Motoyama, T.; Sekiya, M. Chem. Pharm. Bull. 1983, 31, 3939.
4. Carpino, L. A.; Sadat-Aalaee, D.; Chao, H. G.; DeSelms, R. H. J. Am. Chem. Soc. 1990, 112, 9651
5. Carpino, L. A.; Mansour, E. M. E.; Sadat-Aalaee, D. J. Org. Chem 1991, 56, 2611.
6. Popowski, E.; Franz, K. Z. Chem 1979, 19, 103.
7. The syn and anti relationships have been assigned based on NOE signals measured between the 2-H and the 5-H of selected molecules.
8. The α-silyl imines were prepared by stirring trimethylsilylmethylamine and the appropriate ketone or aldehyde in diethyl ether, over activated of 4 Å molecular sieves, for 24 h or more. The imines were isolated by filtration and concentration of the resulting filtrate by rotary evaporation. The unstable imines were used as isolated, as they could not be purified further by distillation or chromatography.
9. 3-imidazoline precursor) and to have the smaller imine substituent cis to the chain (steric considerations).
10. -1.