New technology for the preparation of chiral compounds in organic chemistry is an area of intense developments, due to the concern that many chiral drugs are consumed as racemic mixtures with the potential toxic effects caused by the other enantiomer. Chiral amines, amino alcohols and amino acids are important organic compounds used as building blocks for the synthesis of many pharmaceutical products, and auxiliaries in a variety of enantioselective organic preparations. The design of new methodologies for the enantioselective synthesis of enantiopure compounds with biological activity will be the main purpose of this project. Through our previous research work, we have developed new procedures for primary phenylalkylamine synthesis with modest to good optical purity via the reduction of N-substituted organometallic imino derivatives using known chiral organoborane reagents. Presently, we envision the application of the developed methodology for the preparation of amines and amino alcohols. Besides, the synthesis of novel chiral aminoborohydrides generated by the alpha deprotonation of chiral amine-borane complexes with n-BuLi or LDA for the reduction of imine and/or carbonyl groups, will be proposed. These reagents offer higher reactivity and a better stereochemical control since other competing reducing species are not present. Representative pro-chiral imines and aromatic ketoimines will be reduced with the proposed chiral agents and their enantioselectivity studied under various reaction conditions. Based on the results of the alpha-alkylation of O-TBS acetophenone oximes, asymmetric induction for the preparation of non- racemic products will be attempted using chiral amides as bases, or chiral catalysts, such as 1,3,2-oxazaborolidines. The chiral deprotonation of racemic primary amines with acidic alpha-protons at benzylic positions and amino acids, will be studied since this new area offer great value for the preparation of biological active compounds. The proposed synthetic strategies will be focused on the development of new methods for the preparations of homochiral compounds used as intermediaries of reagents for the synthesis of important pharmacological products.
| Gawronski, Katerina A B; Kim, Junhyong (2017) Single cell transcriptomics of noncoding RNAs and their cell-specificity. Wiley Interdiscip Rev RNA 8: |
| Falk, Samantha J; Lee, Jaehyoun; Sekulic, Nikolina et al. (2016) CENP-C directs a structural transition of CENP-A nucleosomes mainly through sliding of DNA gyres. Nat Struct Mol Biol 23:204-208 |
| Falk, Samantha J; Guo, Lucie Y; Sekulic, Nikolina et al. (2015) Chromosomes. CENP-C reshapes and stabilizes CENP-A nucleosomes at the centromere. Science 348:699-703 |
| Sanchez-Cruz, Pedro; Santos, Areli; Diaz, Stephany et al. (2014) Metal-independent reduction of hydrogen peroxide by semiquinones. Chem Res Toxicol 27:1380-6 |
| Piñero-Santiago, Luis E; García, Carmelo; Lhiaubet-Vallet, Virginie et al. (2013) Photooxidation mechanism of levomepromazine in different solvents. Photochem Photobiol 89:1479-89 |
| Bryant, Jessica M; Meyer-Ficca, Mirella L; Dang, Vanessa M et al. (2013) Separation of spermatogenic cell types using STA-PUT velocity sedimentation. J Vis Exp : |
| Castillo, Betzaida; Bromberg, Lev; López, Xaira et al. (2012) Intracellular Delivery of siRNA by Polycationic Superparamagnetic Nanoparticles. J Drug Deliv 2012:218940 |
| Sanchez-Cruz, Pedro; Dejesus-Andino, Francisco; Alegria, Antonio E (2012) Roles of hydrophilicities and hydrophobicities of dye and sacrificial electron donor on the photochemical pathway. J Photochem Photobiol A Chem 236:54-60 |
| Stepanenko, Viatcheslav; de Jesús, Melvin; Garcia, Carmelo et al. (2012) Synthesis and stability of new spiroaminoborate esters. Tetrahedron Lett 53:910-913 |
| Bansal, Vibha; Delgado, Yamixa; Legault, Marc et al. (2012) Low operational stability of enzymes in dry organic solvents: changes in the active site might affect catalysis. Molecules 17:1870-82 |
Showing the most recent 10 out of 65 publications
