56099-75-3Relevant academic research and scientific papers
Pd-Catalysed oxidative carbonylation of α-amino amides to hydantoins under mild conditions
Botla, Vinayak,Carfagna, Carla,Della Ca, Nicola,Gabriele, Bartolo,Maestri, Giovanni,Mancuso, Raffaella,Montanari, Luca,Motti, Elena,Voronov, Aleksandr
supporting information, p. 294 - 297 (2022/01/06)
The first example of palladium-catalysed oxidative carbonylation of unprotected α-amino amides to hydantoins is described here. The selective synthesis of the target compounds was achieved under mild conditions (1 atm of CO), without ligands and bases. The catalytic system overrode the common reaction pathway that usually leads instead to the formation of symmetrical ureas.
Synthesis of Chiral Hydantoins and Thiazolidinediones via Iridium-Catalyzed Asymmetric Hydrogenation
Li, Jing,Nie, Yu,Yuan, Qianjia,Zhang, Wanbin
supporting information, (2022/01/31)
Herein, we report an iridium-catalyzed asymmetric hydrogenation of hydantoin and thiazolidinedione derived exocyclic alkenes using our developed BiphPHOX as a ligand. The transformation shows good functional group tolerance, and gives the hydrogenated pro
Synthesis of hydantoins from enantiomerically pure α-amino amides without epimerization
Zhang, Dun,Xing, Xuechao,Cuny, Gregory D.
, p. 1750 - 1753 (2007/10/03)
A method for the preparation of enantiomerically pure hydantoins from optically pure α-amino amides utilizing triphosgene is described. We also propose that the racemization observed with 1,1′-carbonyldiimidazole (CDI) for this type of reaction is due to
Chemical Racemization of 5-Benzylhydantoin
Lazarus, Robert A.
, p. 4755 - 4757 (2007/10/02)
The chemical racemization of L-5-benzylhydantoin (L-5BH) at 37 deg C has been investigated in H2O from pH 6 to 14.The pH-rate profile demonstrates hydroxide catalysis on both the free base and free acid form (or the kinetically equivalent water catalysis on the free base form) of L-5BH.In addition the reaction is subject to buffer catalysis by phosphate, Tris, and carbonate.Evidence is presented for a mechanism involving general base catalysis based upon comparison of the second-order buffer-catalyzed rate constants for L-5BH with those obtained for L-5-benzyl-3-methylhydantoin (L-5B-3MH).A Broensted plot yields a βgb = 0.59 for L-5BH and βgb = 0.51 for L-5B-3MH, implying that the proton at carbon 5 is approximately halfway between the hydantoin and the buffer species in the transition state of the racemization reaction.
