Synthesis of amino acid derived imidazolidinium salts as new NHC precatalysts

Dealing at Arm's Length: Catalysis with N‐Heterocyclic Carbene Ligands Bearing Anionic Tethers

“…Chiral amino alcohol based tethered NHC ligand precursors such as 222 , of the type used for copper(I)‐catalyzed conjugate additions (compare Section 3.2), have also been used as organocatalysts for the umpolung of cinnamaldehyde ( 223 ) and subsequent cross‐annulation with trifluoroacetophenone ( 224 ) . The corresponding chiral lactone was obtained as a mixture of diastereomers ( 225 and 226 in a ratio of 77:23) with up to 75:25 e.r .…”

2,2,2-Trifluoroethyl Chlorooxoacetate—Universal Reagent for One-Pot Parallel Synthesis of N1-Aryl-N2-alkyl-Substituted Oxamides

“…Following the concept, we have developed parallel synthesis methods to various drug-like compounds and building blocks with a saturated skeleton including aliphatic sulfonamides, unsymmetrical aliphatic ureas and aliphatic secondary amines. , One of our recent projects to implement the concept was focused on an N 1 -aryl- N 2 -alkyl-substituted oxamide motif. This fragment has found its application in medicinal and synthetic organic chemistry: potential human immunodeficiency virus (HIV-1) entry inhibitors − and antimalarial drugs, − N -heterocyclic carbene (NHC) precatalysts including modifications of the Grubbs’ second generation catalyst, − and other bioactive compounds − are derivatives of the unsymmetrical oxamides (Figure ). Despite growing interest in sized libraries of these oxamides, suitable methods for their parallel synthesis have remained unknown.…”