104261-87-2Relevant academic research and scientific papers
Synthesis and anticancer activity of conformationally constrained Smac mimetics containing pseudo β turns
Baravkar, Sachin B.,Wagh, Mahendra A.,Paul, Debasish,Santra, Manas,Sanjayan, Gangadhar J.
, p. 3473 - 3476 (2018)
Herein, we report synthesis and in vitro anticancer activity of conformationally constrained Smac mimetics containing reverse turn inducing motifs “Ant-Pro” and “sAnt-Pro”. The synthesis of Smac analogs with diverse hydrophobic groups at the C-
Asymmetric intramolecular Michael reaction catalyzed by proline-derived small anilides
Kikuchi, Makoto,Inagaki, Tomohiko,Nishiyama, Hisao
, p. 1075 - 1078 (2007)
Simple proline-derived anilide-catalyzed asymmetric intramolecular Michael reaction was described. Chiral cyclic ketoaldehydes were obtained from acyclic formyl enones in excellent yields with good stereoselectivity. The reaction proceeded in exceptionall
Use of amino amides derived from proline as chiral ligands in the ruthenium(II)-catalyzed transfer hydrogenation reaction of ketones
Rhyoo, Hae Yoon,Yoon, Young-Ae,Park, Hee-Jung,Chung, Young Keun
, p. 5045 - 5048 (2001)
We developed an efficient, easily available, and easy to use proline amide-based ruthenium(II) catalysts for the asymmetric hydride transfer reduction of prochiral ketones and e.e.s up to 98.8% have been measured.
Transfer hydrogenation reactions catalyzed by chiral half-sandwich Ruthenium complexes derived from Proline
Pandia Kumar, Arun Kumar,Samuelson, Ashoka G
, p. 1405 - 1415 (2016)
Chiral ruthenium half-sandwich complexes were prepared using a chelating diamine made from proline with a phenyl, ethyl, or benzyl group, instead of hydrogen on one of the coordinating arms. Three of these complexes were obtained as single diastereoisomers and their configuration identified by X-ray crystallography. The complexes are recyclable catalysts for the reduction of ketones to chiral alcohols in water. A ruthenium hydride species is identified as the active species by NMR spectroscopy and isotopic labelling experiments. Maximum enantio-selectivity was attained when a phenyl group was directly attached to the primary amine on the diamine ligand derived from proline. [Figure not available: see fulltext.]
Enantiomerically pure cyclopalladated diazaphospholidine
Dunina, Valery V.,Gorunova, Olga N.,Stepanova, Valeriya A.,Zykov, Pavel A.,Livantsov, Michail V.,Grishin, Yuri K.,Churakov, Andrey V.,Kuz'mina, Lyudmila G.
, p. 2011 - 2015 (2007)
Enantiomerically pure (S)-2-(anilinomethyl)pyrrolidine (S)-2 was obtained from (S)-proline using a modified four-step procedure in a total yield of 56%. Diamine (S)-2 was converted to diazaphospholidine (S)-1 using oTolP(NMe2)2
Dynamic thermodynamic and dynamic kinetic resolution of 2-lithiopyrrolidines
Coldham, Iain,Dufour, Samuel,Haxell, Thomas F. N.,Patel, Jignesh J.,Sanchez-Jimenez, Graciela
, p. 10943 - 10951 (2006)
Dynamic resolution has been studied as a method for the asymmetric synthesis of 2-substituted pyrrolidines. Highly enantioselective electrophilic substitutions of racemic 2-lithiopyrrolidines in the presence of a chiral ligand have been achieved. The organolithium compounds were prepared by tin-lithium exchange from the corresponding tributylstannanes and n-butyllithium or by deprotonation of N-(tert-butyloxycarbonyl)-pyrrolidine with sec-butyllithium. A range of N-substituents and chiral ligands were investigated for the dynamic resolution. Electrophilic quench of the resolved diastereomeric 2-lithiopyrrolidine-chiral ligand complexes provided the enantiomerically enriched 2-substituted pyrrolidines. With N-alkyl derivatives, the resolution occurs conveniently at (or just below) room temperature and either enantiomer of the product can be formed by appropriate choice of the chiral ligand. The asymmetric induction occurs as a result of a thermodynamic preference for one of the diastereomeric complexes. The minor complex was found to have a faster rate of reaction with the electrophile. The use of N-allylic derivatives provides a means to prepare the N-unsubstituted pyrrolidine products. Best results were obtained with the N-2,3-dimethylbut-2-enyl derivative, and this N-substituent could be cleaved using 1-chloroethyl chloroformate. With N-Boc-2- lithiopyrrolidine, the enantioselectivity arises by a kinetic resolution and high levels of asymmetric induction in the presence of excess n-butyllithium can be obtained. Dynamic kinetic resolution of the N-Boc derivative is limited in the scope of electrophile that can be used.
Synthesis of Cyanuric Chloride based Chiral Reagent for RP-HPLC Enantioseparation of (RS)-Propranolol
Al-Shehri, H. S.,Alwera, S.,Alwera, V.,Joshi, K. K.,Nilugal, K. C.
, p. 376 - 382 (2022/01/24)
In this work, four cyanuric chloride based chiral reagents were prepared via nucleophile substitution of chlorine atom by L-proline derivatives and characterized by UV, FT-IR, HRMS, NMR and elemental analysis. Racemic propranolol was chosen for the chiral
Design, synthesis, and insecticidal activities of novel diamide derivatives with alpha-amino acid subunits
Chen, Rui-Jia,Wang, Jun-Jie,Han, Li,Gu, Yu-Cheng,Xu, Zhi-Ping,Cheng, Jia-Gao,Shao, Xu-Sheng,Xu, Xiao-Yong,Li, Zhong
supporting information, p. 1429 - 1436 (2021/05/06)
A series of diamide derivatives containing α-amino acids were designed and synthesized. These compounds were evaluated for their insecticidal activities against Plutella xylostella, Mythimna separate, Myzus persicae, and Tetranychus cinnabarinus. Most of the title compounds containing an l-phenylglycine skeleton were endowed with good activities at the concentration of 500 mg·L?1. Compounds (R)-A6 showed a potential value for further optimization as an insecticidal lead with the LC50 value of 86.8 mg·L?1.
New small γ-turn type: N -primary amino terminal tripeptide organocatalyst for solvent-free asymmetric aldol reaction of various ketones with aldehydes
Begum, Zubeda,Kwon, Eunsang,Nakano, Hiroto,Okuyama, Yuko,Seki, Chigusa,Takeshita, Mitsuhiro,Thiyagarajan, Rajkumar,Tokiwa, Michio,Tokiwa, Suguru,Uwai, Koji
, p. 38925 - 38932 (2021/12/20)
New small γ-turn type N-primary amino terminal tripeptides were synthesized and their functionality as an organocatalyst was examined in the asymmetric aldol reaction of various ketones with different aromatic aldehydes under solvent-free neat conditions to afford the desired chiral anti-aldol products in good to excellent chemical yields, diastereoselectivities and enantioselectivities (up to 99%, up to syn?:?anti/13?:?87 dr, up to 99% ee). This journal is
Chiral azo-heterocyclic carbene precursor compound with bicyclic framework and preparation method thereof
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Paragraph 0062; 0063; 0064; 0065; 0070; 0072; 0073, (2019/01/22)
The invention discloses a chiral azo-heterocyclic carbene precursor compound with a bicyclic framework and a preparation method thereof. A series of the chiral azo-heterocyclic carbene precursor compound with the bicyclic framework is obtained by taking c
