One of the most difficult problems in the preparation of medicinal agents on the laboratory or industrial scale is the control of stereochemistry and in particular the preparation of enantiomerically pure compounds. One of the most dramatic examples of the importance of chirality control was the use of the drug thalidomide, which was manufactured and sole as a racemic mixture. One optical isomer produced the desired therapeutic effect, while the enantiomer, which was assumed to be pharmacologically inert, led to fetal deformities. Because of dramatic differences in pharmacological effects that enantiomers can produce it is likely that all future drugs that contain chiral centers will be sold as only the desired therapeutically active enantiomer. Transition metal organometallic complexes are widely utilized to efficiently catalyze organic transformations on both the laboratory and industrial scale. There is tremendous potential for using chiral organometallic complexes to carry out enantioselective transformations. However, a major hurdle that has prevented chiral catalysis from fulfilling this potential has been the lack of readily available enantiomerically pure organometallic complexes.
The aims of this project are to prepare enantiomerically pure chiral substituted tetramethylcyclopentadienyl ligands and enantiomerically pure chiral bridged cyclopentadienyl ligands, and to utilize these new enantiomerically pure chiral ligands to prepare new chiral group IV transition metal complexes. We will then examine the potential of these new chiral group IV transition metal complexes to carry out stoichiometric and catalytic enantioselective organic synthesis, with the aim of developing methodologies that can be applied to the synthesis of enantiomerically pure medicinal agents.
|Ifere, Godwin O; Equan, Anita; Gordon, Kereen et al. (2010) Cholesterol and phytosterols differentially regulate the expression of caveolin 1 and a downstream prostate cell growth-suppressor gene. Cancer Epidemiol 34:461-71|
|Mariam, Yitbarek H; Musin, Ryza N (2008) Transition from moderate to strong hydrogen bonds: its identification and physical bases in the case of O-H...O intramolecular hydrogen bonds. J Phys Chem A 112:134-45|
|Kimbro, K Sean; Duschene, Kaitlin; Willard, Margeret et al. (2008) A novel gene STYK1/NOK is upregulated in estrogen receptor-alpha negative estrogen receptor-beta positive breast cancer cells following estrogen treatment. Mol Biol Rep 35:23-7|
|Chu, Qinghui; Pang, Yi (2004) Vibronic structures in the electronic spectra of oligo(phenylene ethynylene): effect of m-phenylene to the optical properties of poly(m-phenylene ethynylene). Spectrochim Acta A Mol Biomol Spectrosc 60:1459-67|
|Sannigrahi, Biswajit; McGeady, Paul; Khan, Ishrat M (2004) Helical poly(3-methyl-4-vinylpyridine)/amino acid complexes: preparation, characterization, and biocompatibility. Macromol Biosci 4:999-1007|
|Liang, Sidney; Bu, Xiu R (2002) Tertiary pentyl groups enhance salen titanium catalyst for highly enantioselective trimethylsilylcyanation of aldehydes. J Org Chem 67:2702-4|
|Vanderveer, Donald; Colon, Marisabel Lebron; Bu, Xiu R (2002) Crystal structure of a chiral Ni complex: (R,R)-N,N'-bis(3-t-butylsalicylidene)-1,2-cyclohexanediaminonickel(II). Anal Sci 18:1283-4|
|Musey, Paul I; Ibim, Sobrasua M; Talukder, Niranjan K (2002) Development of artificial blood vessels: seeding and proliferation characteristics of endothelial and smooth muscle cells on biodegradable membranes. Ann N Y Acad Sci 961:279-83|
|Chiang, C F; Okou, D T; Griffin, T B et al. (2001) Green fluorescent protein rendered susceptible to proteolysis: positions for protease-sensitive insertions. Arch Biochem Biophys 394:229-35|
|Johnson, K P; Rowe, G C; Jackson, B A et al. (2001) Novel antineoplastic isochalcones inhibit the expression of cyclooxygenase 1,2 and EGF in human prostate cancer cell line LNCaP. Cell Mol Biol (Noisy-le-grand) 47:1039-45|
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