Silylformates are emerging surrogates of hydrosilanes, able to reduce carbonyl groups in transfer hydrosilylation reactions, with the concomitant release of CO2. In this work, a new reactivity is revealed for silylformates, in the presence of imines. Using ruthenium catalysts, and lithium iodide as a co-catalyst, imines are shown to undergo hydrocarboxysilylation by formal insertion of CO2 to the N-Si bond of silyl amine to yield silyl carbamates in excellent yields.
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Silylformates are emerging surrogates of hydrosilanes, able to reduce carbonyl groups in transfer hydrosilylation reactions, with the concomitant release of CO2. In this work, a new reactivity is revealed for silylformates, in the presence of imines. Using ruthenium catalysts, and lithium iodide as a co-catalyst, imines are shown to undergo hydrocarboxysilylation by formal insertion of CO2 to the N-Si bond of silyl amine to yield silyl carbamates in excellent yields.
View Article and Find Full Text PDFOxime-functionalized anti-insecticide fabric reduces insecticide exposure through dermal and nasal routes, and prevents insecticide-induced neuromuscular-dysfunction and mortality.
Nat Commun
June 2024
Institute for Stem Cell Science and Regenerative Medicine (DBT-inStem), GKVK Post, Bellary Road, Bangalore, 560065, Karnataka, India.
Farmers from South Asian countries spray insecticides without protective gear, which leads to insecticide exposure through dermal and nasal routes. Acetylcholinesterase plays a crucial role in controlling neuromuscular function. Organophosphate and carbamate insecticides inhibit acetylcholinesterase, which leads to severe neuronal/cognitive dysfunction, breathing disorders, loss of endurance, and death.
View Article and Find Full Text PDFLewis-Base-Catalyzed -Allylation of Silyl Carbamate Latent Pronucleophiles with Allylic Fluorides.
Org Lett
December 2023
Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstrasse 10, 07743 Jena, Germany.
Silyl carbamates, latent pronucleophile surrogates of carbamates, undergo allylation using allylic fluorides in the presence of common Lewis base catalysts. The reactions are rendered enantioselective in the presence of chiral Lewis base catalysts and produce suitably protected derivatives of enantioenriched chiral β-amino acids. The design of the latent pronucleophile featuring both a silyl group and an electron-deficient carbamate is instrumental in lowering the nucleophilicity of nitrogen and enabling enantioselective allylation in the presence of chiral cinchona alkaloid-based catalysts.
View Article and Find Full Text PDFArticle Synopsis
- Tag-assisted liquid-phase peptide synthesis (LPPS) is crucial for pharmaceutical discovery, and incorporating simple silyl groups as hydrophobic tags enhances peptide synthesis.
- New super silyl-based groups (tris(trihexylsilyl)silyl and propargyl super silyl) were developed to improve solubility and reactivity during LPPS, allowing for efficient peptide synthesis.
- These groups are compatible with various chemistry methods (Cbz, Fmoc, and Boc) and have proven effective in synthesizing the peptide Nelipepimut-S with fewer preparation steps than previous methods.
l-Amino Acid Based Phenol- and Catechol-Functionalized Poly(ester-urethane)s for Aromatic π-Interaction Driven Drug Stabilization and Their Enzyme-Responsive Delivery in Cancer Cells.
ACS Appl Bio Mater
November 2022
Department of Chemistry, Indian Institute of Science Education and Research (IISER Pune), Dr. Homi Bhabha Road, Pune 411008, Maharashtra, India.
Exploiting aromatic π-interaction for the stabilization of polyaromatic anticancer drugs at the core of the polymer nanoassemblies is an elegant approach for drug delivery in cancer research. To demonstrate this concept, here we report one of the first attempts on enzyme-responsive polymers from aryl-unit containing amino acid bioresources such as l-tyrosine and 3,4-dihydroxy-l-phenylalanine (l-DOPA). A silyl ether protection strategy was adopted to make melt polymerizable monomers, which were subjected to solvent free melt polycondensation to produce silyl-protected poly(ester-urethane)s.
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