A5088018163- Catalytic C–H Functionalization Methods
- Carbohydrate Chemistry and Synthesis
- Alkaloids: synthesis and pharmacology
- Enzyme Production and Characterization
- Synthesis and Catalytic Reactions
- Synthesis of Organic Compounds
- Sulfur-Based Synthesis Techniques
- Radical Photochemical Reactions
- Chemical synthesis and alkaloids
University of Colorado Boulder
2017-2018
Stereoselective manipulations at the C1 anomeric position of saccharides are one central goals preparative carbohydrate chemistry. Historically, majority reactions forming a bond with carbon has focused on nucleophiles saccharide donors equipped leaving group. Here, we describe novel approach to stereoselective synthesis C-aryl glycosides capitalizing highly stereospecific reaction nucleophiles. First, methods for preparation stannanes have been developed and optimized afford both anomers...
We report a stereoretentive cross-coupling reaction of configurationally stable nucleophiles with disulfide and N-sulfenylsuccinimide donors promoted by Cu(I). demonstrate the utility this method in synthesis thioglycosides derived from simple alkyl aryl thiols, thioglycosides, glycodiversification cysteine residues peptides. These reactions operate well carbohydrate substrates containing common protective groups reagents free hydroxyl secondary amide functionalities under standardized...
A stereospecific cross-coupling reaction of anomeric nucleophiles with diaryliodonium triflates resulting in the synthesis aryl C-glycosides is reported. This process capitalizes on a stereoretentive configurationally stable C1 stannanes and promoted by palladium catalyst presence bulky phosphine ligand that suppresses undesired β-elimination. The utility this has been demonstrated preparation series derived from common saccharides exclusive transfer configuration nucleophile to product,...
A series of cyclic C-glycosides were synthesized using the palladium-catalyzed stereoretentive intramolecular glycosylation aryl iodides by employing a bulky phosphine ligand. variety functional groups are tolerated in reaction, and enantioenriched anomeric nucleophiles could be coupled without erosion optical purity. This study offers unified method to access both cis- trans-fused rings capitalizing on nature Stille reaction. In addition, competition experiments for intermolecular...