An enantioselective route to four tricyclic amino acids and N-tosylamides, composed of a central norbornane framework with a 2-endo,3-endo-annelated pyrrolidine ring and a 5-endo-C₁ or -C₂ side chain, has been developed. A key intermediate was the chiral, N-Boc-protected ketone (1R,2S,6S,7R)-4-azatricyclo[5.2.1.0²,⁶]decan-8-one, available from inexpensive endo-carbic anhydride in five steps and...

The synthesis, complexation properties and catalytic activities under phase-transfer (PT) conditions of differently substituted cyclohexapeptoids are reported. Association constants, for small cationic alkali, and catalytic performances, in a model nucleophilic substitution, are comparable to those of representative crown ethers. Noteworthy, the N-[2-(2-methoxyethoxy)ethyl] side chain derivativ...

In recent decades, the increasing prevalence of age-associated neurodegenerative diseases has underscored the need for targeted therapeutic strategies and novel diagnostics. Peptide-based neurotherapeutics offer high specificity and tolerability but are limited by proteolytic degradation in vivo. Peptoids, or N-substituted glycines, are versatile peptidomimetics that evade proteolytic degradati...

The development of catalytic tools for the late-stage modification amino acids within a peptide framework is challenging task capital importance. Herein, we report Ru-catalyzed C(sp2)?H hydroxylation collection Tyr-containing di- and tripeptides featuring use carbamate as removable directing group PhI(OCOCF3)2 (PIFA) oxidant. This air-compatible tagging technique reliable, scalable provides acc...