65462-94-4Relevant academic research and scientific papers
Photochemical Deracemization at sp3-Hybridized Carbon Centers via a Reversible Hydrogen Atom Transfer
Bach, Thorsten,Breitenlechner, Stefan,Gro?kopf, Johannes,Plaza, Manuel,Seitz, Antonia,Storch, Golo
, p. 21241 - 21245 (2021/12/27)
A photochemical deracemization of 5-substituted 3-phenylimidazolidine-2,4-diones (hydantoins) is reported (27 examples, 69%-quant., 80–99% ee). The reaction is catalyzed by a chiral diarylketone which displays a two-point hydrogen bonding site. Mechanistic evidence (DFT calculations, radical clock experiments, H/D labeling) suggests the reaction to occur by selective hydrogen atom transfer (HAT). Upon hydrogen binding, one substrate enantiomer displays the hydrogen atom at the stereogenic center to the photoexcited catalyst allowing for a HAT from the substrate and eventually for its conversion into the product enantiomer. The product enantiomer is not processed by the catalyst and is thus enriched in the photostationary state.
N1- and N3-Arylations of Hydantoins Employing Diaryliodonium Salts via Copper(I) Catalysis at Room Temperature
Abha Saikia, Raktim,Barman, Dhiraj,Dutta, Anurag,Jyoti Thakur, Ashim
, p. 400 - 410 (2020/12/17)
Copper(I)-catalyzed N-arylation (both N1- and N3-) of hydantoins with diaryliodonium salts as aryl partners at room temperature is reported. The transformation allows diverse scopes on both hydantoins and diaryliodonium salts deliver
Quantitative Modeling of Bis(pyridine)silver(I) Permanganate Oxidation of Hydantoin Derivatives: Guidelines for Predicting the Site of Oxidation in Complex Substrates
Bischoff, Amanda J.,Nelson, Brandon M.,Niemeyer, Zachary L.,Sigman, Matthew S.,Movassaghi, Mohammad
supporting information, p. 15539 - 15547 (2017/11/06)
The bis(pyridine)silver(I) permanganate promoted hydroxylation of diketopiperazines has served as a pivotal transformation in the synthesis of complex epipolythiodiketopiperazine alkaloids. This late-stage C-H oxidation chemistry is strategically critical to access N-acyl iminium ion intermediates necessary for nucleophilic thiolation of advanced diketopiperazines en route to potent epipolythiodiketopiperazine anticancer compounds. In this study, we develop an informative mathematical model using hydantoin derivatives as a training set of substrates by relating the relative rates of oxidation to various calculated molecular descriptors. The model prioritizes Hammett values and percent buried volume as key contributing factors in the hydantoin series while correctly predicting the experimentally observed oxidation sites in various complex diketopiperazine case studies. Thus, a method is presented by which to use simplified training molecules and resulting correlations to explain and predict reaction behavior for more complex substrates.
Asymmetric and diastereoselective Mannich reactions using hydantoin as a chiral auxiliary
Li, Xuan-Ran,Lu, Cui-Fen,Chen, Zu-Xing,Li, Yan,Yang, Gui-Chun
, p. 1380 - 1384,5 (2020/09/16)
The Mannich reaction of titanium enolates of a chiral hydantoin with various aldimines smoothly occurred in good yields and with high anti-diastereoselectivity. The Mannich adducts can be readily cleaved by alcoholysis to afford several β-amino ester derivatives in good yields and in almost enantiomerically pure form.
A facile method for preparation of optically active hydantoin
Yamaguchi, Jun-Ichi,Harada, Masakazu,Kondo, Takahito,Noda, Takeshi,Suyama, Takayuki
, p. 372 - 373 (2007/10/03)
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
