A5066630686- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Catalytic C–H Functionalization Methods
- Radical Photochemical Reactions
- Catalytic Alkyne Reactions
- Oxidative Organic Chemistry Reactions
- Cyclopropane Reaction Mechanisms
- Vanadium and Halogenation Chemistry
- Synthesis and Catalytic Reactions
- Asymmetric Hydrogenation and Catalysis
- Sulfur-Based Synthesis Techniques
- Metal-Catalyzed Oxygenation Mechanisms
- Click Chemistry and Applications
- Advanced Photocatalysis Techniques
- Nanomaterials for catalytic reactions
- Organoselenium and organotellurium chemistry
Princeton University
2021-2023
Oxford Research Group
2019-2021
University of Oxford
2021
University of Illinois Urbana-Champaign
2019
The replacement of aryl rings with saturated carbocyclic structures has garnered significant interest in drug discovery due to the potential for improved pharmacokinetic properties upon substitution. In particular, 1,3-difunctionalized bicyclo[1.1.1]pentanes (BCPs) have been widely adopted as bioisosteres parasubstituted arene rings, appearing a number lead pharmaceutical candidates. However, despite value 2-substituted BCPs replacements ortho- or meta-substituted general and rapid syntheses...
Ynamides are accessed via copper-catalyzed coupling of Grignard or organozinc nucleophiles with chloroynamides, formed in situ from 1,2-dichloroenamides. The reaction exhibits a broad substrate scope, is readily scaled, and overcomes typical limitations ynamide synthesis such as the use ureas, carbamates, bulky aromatic amide derivatives. This modular approach contrasts previous routes by installing both N- C-substituents nucleophilic components.
Yndiamides, underexplored cousins of ynamides, offer rich synthetic potential as doubly nitrogenated two carbon building blocks. Here we report a gold-catalyzed oxidative functionalization yndiamides to access unnatural amino acid derivatives, using wide range nucleophiles source the side chain. The transformation proceeds under mild conditions, is highly functional group tolerant, and displays excellent regioselectivity through subtle steric differentiation yndiamide nitrogen atom substituents.
The replacement of benzene rings with sp3-hybridized bioisosteres in drug candidates generally improves pharmacokinetic properties while retaining biological activity. Rigid, strained frameworks such as bicyclo[1.1.1]pentane and cubane are particularly well-suited since the ring strain imparts high bond strength thus metabolic stability on its C–H bonds. Cubane is ideal bioisostere it provides closest geometric match to benzene. At present, however, all cubanes design, like almost...
The replacement of aryl rings with C(sp3)-rich structures has garnered significant interest in drug discovery due to the potential for improved pharmacokinetic properties upon substitution. In particular, 1,3-difunctionalized bicyclo[1.1.1]pentanes (BCPs) have been widely adopted as bioisosteres para-substituted arene rings, appearing a number lead pharmaceutical candidates. Due their medicinal importance, multiple methods developed efficiently synthesize these BCPs. However, despite value...
Abstract Yndiamides, N,N-disubstituted alkynes, are versatile building blocks for the synthesis of nitrogen-containing organic molecules. Unlike ynamides, relatives that inherently polarized by a single nitrogen substituent, their pseudo-symmetric nature renders regioselective reactions challenging. Here we report investigations into regioselective addition Brønsted acids to non-symmetric yndiamides, reaction delivers N,O,N- and N,S,N-trisubstituted ketene acetals with excellent regio-...