17131-52-1Relevant articles and documents
Effective synthesis of non-racemic prenalterol based on spontaneous resolution of 3-(4-hydroxyphenoxy)propane-1,2-diol
Bredikhina, Zemfira A.,Kurenkov, Alexey V.,Bredikhin, Alexander A.
, p. 198 - 199 (2019/04/25)
Spontaneous resolution of rac-3-(4-hydroxyphenoxy)propane-1,2-diol has been successfully used in the synthesis of both enantiomers of chiral drug prenalterol.
Asymmetric Hydrolytic and Aminolytic Kinetic Resolution of Racemic Epoxides using Recyclable Macrocyclic Chiral Cobalt(III) Salen Complexes
Tak, Rajkumar,Kumar, Manish,Menapara, Tusharkumar,Gupta, Naveen,Kureshy, Rukhsana I.,Khan, Noor-ul H.,Suresh
supporting information, p. 3990 - 4001 (2017/11/22)
New chiral macrocyclic cobalt(III) salen complexes were synthesized and used as catalyst for the asymmetric kinetic resolution (AKR) of terminal epoxides and glycidyl ethers with aromatic/aliphatic amines and water as nucleophiles. This is the first occasion where a Co(III) salen complex demonstrated its ability to catalyze AKR as well as hydrolytic kinetic resolution (HKR) reactions. Excellent enantiomeric excesses of the epoxides, the corresponding amino alcohols and diols (upto 99%) with quantitative yields were achieved by using the chiral Co(III) salen complexes in dichloromethane at room temperature. This protocol was further extended for the synthesis of two important drug molecules, i.e., (S)-propranolol and (R)-naftopidil. The catalytic system was also explored for the synthesis of chirally pure diols and chiral cyclic carbonates using carbon dioxide as a greener renewable C1 source. The catalyst was recycled for upto 5 catalytic cycles with retention of enantioselectivity. (Figure presented.).
Synthesis and some features of phase behavior of chiral p-alkoxyphenyl glycerol ethers
Fayzullin,Antonovich,Zakharychev,Bredikhina,Kurenkov,Bredikhin
, p. 202 - 209 (2015/04/14)
A series of (S)-3-(4-alkoxyphenoxy)propane-1,2-diols was prepared with the enantiomeric excess 86-92% by Sharpless asymmetric dihydroxylation of 1-alkoxy-4-allyloxybenzenes with an AD-mix-β mixture. R-Enantiomers with enantiomeric excess 97-99% and racemic samples were obtained by reaction of sodium p-substituted phenolates with (R)- and rac-3-chloropropane-1,2-diol. The phase behavior of racemates and scalemates in the produced homolog series of glycerol aryl ethers with hydrocarbon substituents of various length was examined by means of thermomicroscopy. The higher memberes of the homolog series of both racemic and scalemic diols undergo at heating an enantiotropic phase transition to a smectic liquid crystal phase.
Structure-activity relationships of lysophosphatidylserine analogs as agonists of G-protein-coupled receptors GPR34, P2Y10, and GPR174
Ikubo, Masaya,Inoue, Asuka,Nakamura, Sho,Jung, Sejin,Sayama, Misa,Otani, Yuko,Uwamizu, Akiharu,Suzuki, Keisuke,Kishi, Takayuki,Shuto, Akira,Ishiguro, Jun,Okudaira, Michiyo,Kano, Kuniyuki,Makide, Kumiko,Aoki, Junken,Ohwada, Tomohiko
supporting information, p. 4204 - 4219 (2015/06/08)
Lysophosphatidylserine (LysoPS) is an endogenous lipid mediator generated by hydrolysis of membrane phospholipid phosphatidylserine. Recent ligand screening of orphan G-protein-coupled receptors (GPCRs) identified two LysoPS-specific human GPCRs, namely, P2Y10 (LPS2) and GPR174 (LPS3), which, together with previously reported GPR34 (LPS1), comprise a LysoPS receptor family. Herein, we examined the structure-activity relationships of a series of synthetic LysoPS analogues toward these recently deorphanized LysoPS receptors, based on the idea that LysoPS can be regarded as consisting of distinct modules (fatty acid, glycerol, and l-serine) connected by phosphodiester and ester linkages. Starting from the endogenous ligand (1-oleoyl-LysoPS, 1), we optimized the structure of each module and the ester linkage. Accordingly, we identified some structural requirements of each module for potency and for receptor subtype selectivity. Further assembly of individually structure-optimized modules yielded a series of potent and LysoPS receptor subtype-selective agonists, particularly for P2Y10 and GPR174.
Asymmetric hydrolytic kinetic resolution with recyclable polymeric Co(iii)-salen complexes: A practical strategy in the preparation of (S)-metoprolol, (S)-toliprolol and (S)-alprenolol: Computational rationale for enantioselectivity
Roy, Tamal,Barik, Sunirmal,Kumar, Manish,Kureshy, Rukhsana I.,Ganguly, Bishwajit,Khan, Noor-Ul H.,Abdi, Sayed H. R.,Bajaj, Hari C.
, p. 3899 - 3908 (2015/02/19)
A series of chiral polymeric Co(iii)-salen complexes based on a number of achiral and chiral linkers were synthesized and their catalytic performances were assessed in the asymmetric hydrolytic kinetic resolution of terminal epoxides. The effects of the linker were judiciously studied and it was found that in the case of the chiral BINOL-based polymeric salen complex 1, there was an enrichment in catalyst reactivity and enantioselectivity of the unreacted epoxide, particularly in the case of short as well as long chain aliphatic epoxides. Good isolated yields of the unreacted epoxide (up to 46% compared to 50% theoretical yield) along with high enantioselectivity (up to 99%) were obtained in most cases using catalyst 1. Further studies showed that catalyst 1 could retain its catalytic activity for six cycles under the present reaction conditions without any significant loss in activity or enantioselectivity. To show the practical applicability of the above synthesized catalyst we have synthesised some potent chiral β-blockers in moderate yield and high enantioselectivity using complex 1. The DFT (M06-L/6-31+G??//ONIOM(B3LYP/6-31G?:STO-3G)) calculations revealed that the chiral BINOL linker influences the enantioselectivity achieved with Co(iii)-salen complexes. Further, the transition state calculations show that the R-BINOL linker with the (S,S)-Co(iii)-salen complex is energetically preferred over the corresponding S-BINOL linker with the (S,S)-Co(iii)-salen complex for the HKR of 1,2-epoxyhexane. The role of non-covalent C-H?π interactions and steric effects has been discussed to control the HKR reaction of 1,2-epoxyhexane.
One-pot synthesis of aryloxypropanediols from glycerol: Towards valuable chemicals from renewable sources
Truscello, Ada M.,Gambarotti, Cristian,Lauria, Mirvana,Auricchio, Sergio,Leonardi, Gabriella,Shisodia, Suresh U.,Citterio, Attilio
supporting information, p. 625 - 628 (2013/03/29)
Glycerol offers an easy and green route for the synthesis of aryloxypropanediols of known pharmacological activity. Glycerol is selectively converted to aryloxypropanediols in a one-pot reaction, through in situ formed glycerol carbonate, under benign and solvent-free conditions. Catalyst and unreacted reagent can be recycled.
Chiral nanoporous metal-metallosalen frameworks for hydrolytic kinetic resolution of epoxides
Zhu, Chengfeng,Yuan, Guozan,Chen, Xu,Yang, Zhiwei,Cui, Yong
supporting information; experimental part, p. 8058 - 8061 (2012/07/14)
Chiral nanoporous metal-organic frameworks are constructed by using dicarboxyl-functionalized chiral Ni(salen) and Co(salen) ligands. The Co(salen)-based framework is shown to be an efficient and recyclable heterogeneous catalyst for hydrolytic kinetic resolution (HKR) of racemic epoxides with up to 99.5% ee. The MOF structure brings Co(salen) units into a highly dense arrangement and close proximity that enhances bimetallic cooperative interactions, leading to improved catalytic activity and enantioselectivity in HKR compared with its homogeneous analogues, especially at low catalyst/substrate ratios.
Catalysis through temporary intramolecularity: Mechanistic investigations on aldehyde-catalyzed cope-type hydroamination lead to the discovery of a more efficient tethering catalyst
Guimond, Nicolas,MacDonald, Melissa J.,Lemieux, Valerie,Beauchemin, Andre M.
supporting information, p. 16571 - 16577,7 (2020/09/15)
Mechanistic investigations on the aldehyde-catalyzed intermolecular hydroamination of allylic amines using N-alkylhydroxylamines are presented. Under the reaction conditions, the presence of a specific aldehyde catalyst allows formation of a mixed aminal intermediate, which permits intramolecular Cope-type hydroamination. The reaction was determined to be first-order in both the aldehyde catalyst (α-benzyloxyacetaldehyde) and the allylic amine. However, the reaction displays an inverse order behavior in benzylhydroxylamine, which reveals a significant off-cycle pathway and highlights the importance of an aldehyde catalyst that promotes a reversible aminal formation. Kinetic isotope effect experiments suggest that hydroamination is the rate-limiting step of this catalytic cycle. Overall, these results enabled the elaboration of a more accurate catalytic cycle and led to the development of a more efficient catalytic system for alkene hydroamination. The use of 5-10 mol % of paraformaldehyde proved more effective than the use of 20 mol % of α-benzyloxyacetaldehyde, leading to high yields of intermolecular hydroamination products within 24 h at 30 °C.
Asymmetric organocatalytic efficiency of synthesized chiral β-amino alcohols in ring-opening of glycidol with phenols
Aral, Tarik,Karakaplan, Mehmet,Hosgoeren, Halil
experimental part, p. 794 - 802 (2012/08/28)
A series of novel chiral β-amino alcohols 3-5 and 7-10 were synthesized by regioselective ring opening of epoxides and chiral amines with a straightforward method in high yields (up to 99 %). Kinetic resolution of racemic glycidol with phenols was achieved by using chiral amino alcohols as organocatalysts. Amino alcohols 5, 8 and 10 exhibited the highest enantioselectivities with p-cresol, phenol, and p-methoxyphenol by 63, 65, 58 % ee, respectively. The moderate enantioselectivities were observed with catalyst 9b towards all the nucleophiles (34-48 % ee). The ee values of the desired 3-aryloxy-1, 2-diols were determined by HPLC. This study presents an attractive tool for the synthesis of β-blockers and structurally complex molecules.
Enantioselective complexation of chiral lariat crown ethers and chiral primary alkylammonium perchlorates
Koeylue, M. Zafer,Aral, Tarik,Karakaplan, Mehmet,Kocakaya, Safak Oezhan,Hosgoeren, Halil
scheme or table, p. 174 - 179 (2012/05/05)
In order to investigate the enantiomeric recognition abilities toward 2 chiral alkylammonium perchlorates (AmI, AmII) by 1 H-NMR titration method in CDCl3, 4 chiral lariat ethers 8-11 with a (p-methoxyphenoxy) methyl flexible side arm were used. The most effective enantiomeric recognition was obtained by LCEs 9 and 11 toward AmII, by K R/KS 6.58 and KS/KR 6.63, respectively. The effect of macroring size, subunit of macroring, and side arm appeared to have strong influence on the binding ability of these alkylammonium ions. TUeBITAK.
