A5079449946- Asymmetric Synthesis and Catalysis
- Innovative Microfluidic and Catalytic Techniques Innovation
- Chemical Synthesis and Reactions
- Radical Photochemical Reactions
- Chemical Synthesis and Analysis
- Synthetic Organic Chemistry Methods
- Oxidative Organic Chemistry Reactions
- Electrowetting and Microfluidic Technologies
- Peptidase Inhibition and Analysis
- Synthesis and pharmacology of benzodiazepine derivatives
- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Asymmetric Hydrogenation and Catalysis
- Microfluidic and Capillary Electrophoresis Applications
- Protein Degradation and Inhibitors
- Multiple Myeloma Research and Treatments
Boehringer Ingelheim (United States)
2023-2024
Boston University
2018
A short and scalable process for the facile synthesis of chiral spirocyclic isoxazolone 1 was developed demonstrated on a multiple kilogram scale in four steps from readily available starting material 8. To achieve sustainability efficiency, we implemented highly efficient catalytic asymmetric allylic alkylation telescopic chemical process. More than 160 kg were produced as crystalline solid by simple operation with >99:1 er 38% overall yield. The structure further confirmed single-crystal...
A scalable synthesis of the SMARCA2 degrading PROTAC 1 was developed. The linker fragment derived from (S)-citronellol by oxidative cleavage and diastereoselective aryl Grignard addition to a N-tert-butanesulfinyl aldimine for generation chiral amine stereocenter one-pot borylation/Suzuki reaction biaryl formation. dipeptide prepared T3P-mediated coupling hydroxyproline benzyl ester N-Boc tert-leucine followed capping with 1-fluorocyclopropancarboxylic acid hydrolysis. Unification binding...
Abstract [2+2] photocycloaddition of cinnamates, using a previously described cone reactor and bis‐thiourea catalyst, is greatly accelerated by employing liquid–liquid slug flow. In most cases, four‐fold acceleration in reaction time was observed with equivalent or superior yields. This approach has enabled significant improvement the throughput expansion substrate scope to include challenging substrates. It also enabled, our knowledge, first reported direct photodimerization solution...
Commercially and readily available MSTFA [2,2,2-trifluoro-N-methyl-N-(trimethylsilyl)acetamide] was identified as a highly effective TMS (trimethylsilyl) source for the convenient preparation of cyclic acetals under modified Noyori's conditions. The reactions proceeded smoothly mild conditions, affording wide range corresponding with excellent yields in presence catalytic TMSOTf (trimethylsilyl trifluoromethanesulfonate). present method does not require large excess diols that can be...
Asymmetric allylic alkylation (AAA) presents an exceptionally powerful and efficient tool for the rapid synthesis of a diverse range chiral compounds with high yields excellent levels enantioselectivity. To support production ethyl (R)-1-allyl-2-oxocyclohexane-1-carboxylate 1 on large scale, highly practical economical AAA process is desirable. Herein, we report greatly improved reaction protocol by thorough optimization original conditions developed Trost et al. Multiple parameters...
Abstract An improved chemical process has been developed for the synthesis of (S,S)-DACH-Ph Trost ligand. The amidation 2-diphenylphosphinylbenzoic acid and (S,S)-diaminocyclohexane is promoted by stoichiometric CDI catalytic imidazole hydrochloride. resulting product, ligand, isolated as a white solid in 80% yield with >99% ee simple filtration without column chromatography. current facile also demonstrated on kilogram scale.
Abstract The front cover artwork is provided by the Beeler Research Group in Department of Chemistry at Boston University. image depicts a metal halide lamp surrounded length tubing. Inside tubing rendition biphasic flow and simplified depiction simulated circulation patterns within slugs. At top right DFT‐optimized model delta truxinate, highlighting beauty molecules that this system can be used to synthesize. Read full text Article 10.1002/cptc.201800081 .