A series of silyl-substituted amino acids have been synthesized, inserted into peptides, and then employed as precursors for oxidatively generating reactive N-acyliminium ions. Both electrochemical and chemical oxidation procedures have been employed. N-Acyliminium ion generation in a solid-phase substrate as well as application to a small library of functionalized dipeptides has been demonstrated. Limitations in terms of how electron-rich the silyl groups can be as well as the compatibility of multiple silyl groups within a longer peptide are defined.
Parallel electrosynthesis of alpha-alkoxycarbamates, alpha-alkoxyamides, and alpha-alkoxysulfonamides using the spatially addressable electrolysis platform (SAEP)
(2-methoxyphenyl)dimethylsilyl lithium and cuprate reagents offer unique advantages in multistep synthesis
An Oxidative Mannich Cyclization Methodology for the Stereocontrolled Synthesis of Highly Functionalized Piperidines
Basic concepts of "cation pool" and "cation flow" methods and their applications in conventional and combinatorial organic synthesis
Building addressable libraries: the use of electrochemistry for generating reactive Pd(II) reagents at preselected sites on a chip
Structure-reactivity relationships in oxidative carbon-carbon bond forming reactions: a mild and efficient approach to stereoselective syntheses of 2,6-disubstituted tetrahydropyrones
Building addressable libraries: the use of electrochemistry for spatially isolating a heck reaction on a chip
Design, synthesis, and application of azabicyclo[X.Y.0]alkanone amino acids as constrained dipeptide surrogates and peptide mimics
Regioselective incorporation of backbone constraints compatible with traditional solid-phase peptide synthesis
Stereoselective synthesis of amido and phenyl azabicyclic derivatives via a tandem aza Prins-Ritter/Friedel-Crafts type reaction of endocyclic N-acyliminium ions
Microelectrode arrays: a general strategy for using oxidation reactions to site selectively modify electrode surfaces
Expedient synthesis of highly potent antagonists of inhibitor of apoptosis proteins (IAPs) with unique selectivity for ML-IAP
Design of Modified Amine Transfer Reagents Allows the Synthesis of α-Chiral Secondary Amines via CuH-Catalyzed Hydroamination
A novel electrosynthetic system for anodic substitution reactions by using parallel laminar flow in a microflow reactor
Photovoltaic-driven organic electrosynthesis and efforts toward more sustainable oxidation reactions
The Shono-type electroorganic oxidation of unfunctionalised amides. Carbon-carbon bond formation via electrogenerated N-acyliminium ions
Microelectrode arrays and ceric ammonium nitrate: a simple strategy for developing new site-selective synthetic methods
Total synthesis of biseokeaniamides A-C and late-stage electrochemically-enabled peptide analogue synthesis.
An Electrochemical Approach to Designer Peptide α-Amides Inspired by α-Amidating Monooxygenase Enzymes.
Stereoselective capture of N-acyliminium ions generated from α-hydroxy-N-acylcarbamides: direct synthesis of uracils from barbituric acids enabled by SmI2 reduction
Expedient preparation of nazlinine and a small library of indole alkaloids using flow electrochemistry as an enabling technology
Stereoselective Synthesis of Pyrroloisoindolone and Pyridoisoindolone via aza-Prins Cyclization of Endocyclic N-Acyliminium Ions
Synthesis of pyrimido[2,1-a]isoindolone and isoindolo[2,1-a]quinazolinone via intramolecular aza-Prins type reaction.
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