A5049932044- Chemical Synthesis and Analysis
- Catalytic C–H Functionalization Methods
- Organoboron and organosilicon chemistry
- Asymmetric Synthesis and Catalysis
- Signaling Pathways in Disease
- Biochemical and Structural Characterization
- Monoclonal and Polyclonal Antibodies Research
- Catalytic Cross-Coupling Reactions
- Asymmetric Hydrogenation and Catalysis
- Innovative Microfluidic and Catalytic Techniques Innovation
- Crystallization and Solubility Studies
- Oxidative Organic Chemistry Reactions
- Radical Photochemical Reactions
- X-ray Diffraction in Crystallography
- Axial and Atropisomeric Chirality Synthesis
- Protein purification and stability
- Chemical Reactions and Isotopes
Massachusetts Institute of Technology
2024-2025
Boston College
2019-2022
Chestnut Hill College
2020
University of Pennsylvania
2017
An efficient deuteration process of β-amino C–H bonds in various N-alkylamine-based pharmaceutical compounds has been developed. Catalytic reactions begin with the action Lewis acidic B(C6F5)3 and Brønsted basic N-alkylamine, converting a drug molecule into corresponding enamine. The acid/base catalysts also promote dedeuteration acetone-d6 to afford deuterated ammonium ion. Ensuing enamine then leads formation β-deuterated bioactive amines up 99% deuterium incorporation.
An efficient and highly enantioselective Conia-ene-type process has been developed. Reactions are catalyzed by a combination of B(C6F5)3, an N-alkylamine BOX-ZnI2 complex. Specifically, through cooperative action B(C6F5)3 amine, ketones with poorly acidic α-C-H bonds can be converted in situ to the corresponding enolates. Subsequent cyclization involving BOX-ZnI2-activated alkyne leads formation various cyclopentenes up 99% yield 99:1 er.
An efficient catalytic method to convert an α-C–H bond of N-alkylamines into α-C–alkynyl was developed. In the past, such transformations were carried out under oxidative conditions, and enantioselective variants confined tetrahydroisoquinoline derivatives. Here, we disclose a for union trimethylsilyl alkynes, without presence external oxidant promoted through cooperative actions two Lewis acids, B(C6F5)3 Cu-based complex. A variety propargylamines can be synthesized in high diastereo-...
The chemical synthesis of proteins (CSP) has been an essential tool in studying and understanding the role these biological polymers enabling discovery novel classes inhibitors. However, CSP with commercially available synthesizers is typically limited to producing polypeptides about 50 70 amino acids length. Consequently, a wide range protein targets have inaccessible using technologies, or they require cumbersome purification multiple peptide fragments. In this report, we employed powerful...
We disclose a catalytic method for the enantio- and diastereoselective union of alkyl ethers heterodienes. demonstrate that chiral Cu–BOX complex catalyzes efficient oxidation into enol in presence trityl acetate. Then, organocopper promotes stereoselective hetero Diels–Alder reaction between situ generated β,γ-unsaturated ketoesters, allowing rapid access to an array dihydropyran derivatives possessing three vicinal stereogenic centers.
The chemical synthesis of proteins (CSP) has been an essential tool in studying and understanding the role these biological polymers enabling discovery novel classes inhibitors. However, CSP with commercially available synthesizers is typically limited to producing polypeptides about 50 70 amino acids length. Consequently, a wide range protein targets have out reach using technologies or require cumbersome purification multiple peptide fragments. In this report, we employed powerful...
Tumor necrosis factor-alpha (TNF-α) plays a central role in immune response regulation. Due to the correlation between elevated TNF-α production and range of diseases, inhibiting interaction this protein with its native receptors as therapeutic avenue has been thoroughly explored. Despite advancements development lead inhibitors, concerns remain regarding immunogenicity loss activity vivo. To facilitate discovery stable less immunogenic modalities, we describe rapid synthesis protocol that...
We disclose a method for sequential Conia-ene-type cyclization/Negishi coupling the union of alkynyl ketones and aryl iodides. This process is promoted through cooperative actions Lewis acidic B(C6F5)3, ZnI2, Pd-based complex, Brønsted basic amine. The three acid catalysts with potential overlapping functions play their independent roles as activators carbonyl group, alkyne moiety, alkenyl zinc intermediate, respectively. A variety 1,2,3-substituted cyclopentenes can be synthesized high efficiency.
Cooperative actions of two or more Lewis acid and/or base catalysts can be exploited to promote enantioselective transformations that are not readily achieved by a single catalyst system. Nonetheless, undesirable acid-base complexation which occurs in reaction mixture containing the catalysts, substrates, and products often results poor efficiency contrived substrate scope. In this article, we highlight our development multi-catalyst systems facilitate otherwise unreactive C-H bonds...