Solid phase synthesis of aziridine 2-carboxylates

Solid‐Phase Synthesis of Heterocyclic Systems (Heterocycles Containing One Heteroatom)

“…This reaction sequence was adapted to solid phase by Filigheddu and coworkers [2] in a construction of aziridine-containing peptidomimetics (Scheme 22.1). Wang resin esterified with amino acids 1 serves as resinbound amine substrates.…”

Aminolysis of Resin-Bound N-Nosylaziridine-2-carboxylic Acids

“…Aziridines were recently applied in solid-phase synthesis (SPS) of thioglycopeptide derivatives by Gin, van der Donk, and co-workers. , Their approach consisted of ring opening of resin-bound peptide substrates containing aziridine-2-carboxylic acid (Azy-OH) residues with various sulfur nucleophiles, , and ring-opening reactions with selenium nucleophiles were also demonstrated by this group . However, the number of reactions employing resin-bound aziridines is still very limited. − …”

Aziridines in Parallel‐ and Solid‐Phase Synthesis

“…[19,20] Until now, the only reported on-resin syntheses of aziridines utilized the Gabriel-Cromwell reaction between amines and α-bromoacrylates or α-bromoacrylamides. [21] Two strategies denoted as the direct strategy and the reverse strategy were developed for the synthesis of N-alkylated aziridine-2-carboxylic acid (Azy) derivatives on a Wang resin, as out- Scheme 6. lined in Scheme 7. The so-called direct strategy, where α-bromoacryl esters/amides 40 are in solution while the amines are anchored to the Wang resin 41, resulted in resinbound dipeptide analogues 42, which were cleaved to give nine different products of type 43.…”

“…The so-called direct strategy, where α-bromoacryl esters/amides 40 are in solution while the amines are anchored to the Wang resin 41, resulted in resinbound dipeptide analogues 42, which were cleaved to give nine different products of type 43. [21] In the reverse strategy, the amines 44 in solution were subjected to tandem addition-cyclization with resin-bound α-bromoacrylamides 45 to yield twelve N-alkylated aziridine-2-carboxamides 47. Although the compounds produced by these strategies were racemic mixtures, enantiomerically enriched aziridines have been obtained by the Gabriel-Cromwell reaction using a Scheme 7. chiral auxiliary in solution, [22] which may enable future SPS of useful, enantiomerically pure aziridine-2-carboxylic acids.…”