215670-78-3Relevant academic research and scientific papers
A facile method for preparation of optically active hydantoin
Yamaguchi, Jun-Ichi,Harada, Masakazu,Kondo, Takahito,Noda, Takeshi,Suyama, Takayuki
, p. 372 - 373 (2003)
Treatment of N-(4-nitrophenoxycarbonyl)amino acid amide, which was prepared from amino acid amide and 4-nitrophenyl chloroformate, under weakly basic conditions proceeded to afford the corresponding hydantoin. A direct conversion of amino acid amide into
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.
Enantioselective synthesis of 3,5-disubstituted thiohydantoins and hydantoins
Chen, Yu,Su, Li,Yang, Xinying,Pan, Wenyan,Fang, Hao
, p. 9234 - 9239 (2015/11/27)
A mild method to convert optically pure amino acid thiourea and urea derivatives to thiohydantoins and hydantoins, respectively, is described. It provides an efficient way to realize enantioselective synthesis of thiohydantoins and hydantoins with good to high isolated yields and enantiomeric purities. We found that the enantiomeric purities were highly dependent on the reaction conditions including bases, solvents, and temperature.
Synthesis of highly substituted imidazolidine-2,4-dione (Hydantoin) through Tf2O-mediated dual activation of Boc-protected dipeptidyl compounds
Liu, Hui,Yang, Zhimin,Pan, Zhengying
supporting information, p. 5902 - 5905 (2015/01/08)
Highly substituted chiral hydantoins were readily synthesized from simple dipeptides in a single step under mild conditions. This reaction proceeded through the dual activation of an amide and a tert-butyloxycarbonyl (Boc) protecting group by Tf2O-pyridine. This method was successfully applied in the preparation of a variety of biologically active compounds, including drug analogs and natural products.
Boron enolates of a hydantoin chiral auxiliary derived from l-phenylalanine: A versatile tool for asymmetric aldol reactions
Zhang, Ji-Shu,Lu, Cui-Fen,Chen, Zu-Xing,Li, Yan,Yang, Gui-Chun
experimental part, p. 72 - 75 (2012/05/20)
The aldol reactions of boron enolates derived from a hydantoin chiral auxiliary derived from l-phenylalanine occur in good yields with high syn diastereoselectivity. Aldol adduct 4a is readily cleaved by hydrolysis to afford (2S,3S)-3-hydroxy-2-methyl-3-p
Diastereoselective conjugate addition of 1-(α,β-unsaturated acyl)hydantoin with nucleophiles
Yamaguchi, Jun-Ichi,Harada, Masakazu,Narushima, Takao,Saitoh, Asumi,Nozaki, Kanako,Suyama, Takayuki
, p. 6411 - 6415 (2007/10/03)
A diastereomeric conjugate addition of dialkylaluminum chloride to 1-(α,β-unsaturated acyl)hydantoin provided the corresponding alkyl adduct with inducted chirality in the β-position. Treatment of 1-(α,β-unsaturated acyl)hydantoin with Gilman reagent in the presence of Lewis acid also gave the same product. In this reaction, diethylaluminum chloride was the most effective Lewis acid and the absolute configuration of the major adduct at the β-position of acyl group depended on the kinds of existing metals.
Combinatorial chemistry of hydantoins
Boeijen, Astrid,Kruijtzer, John A.W.,Liskamp, Rob M.J.
, p. 2375 - 2380 (2007/10/03)
Access to combinatorial chemistry of hydantoins is provided by convenient and versatile methods for the solid phase synthesis of libraries of 3,5-, 1,3- and 1,3,5-substituted hydantoins. The preparation of trisubstituted hydantoins features a Mitsunobu reaction for introduction of the substituent on N-1.
