130194-42-2Relevant articles and documents
A Green approach towards the synthesis of chiral alcohols using functionalized alginate immobilized Saccharomyces cerevisiae cells
Muthineni, Narmada,Arnipally, Manikanta Swamy,Bojja, Sridhar,Meshram, Harshadas Mitaram,Srivastava, Ajay Kumar,Adari, Bhaskar Rao
, p. 233 - 237 (2016/12/09)
The stereochemistry of the drug molecule is gaining greater therapeutic importance and thus much attention was drawn in synthesis of chiral compounds by the pharmaceutical industry. In this study Saccharomyces cerevisiae cells immobilized on functionalize
Simple 1,3-diamines and their application as ligands in ruthenium(II) catalysts for asymmetric transfer hydrogenation of aryl ketones
Facchetti, Giorgio,Gandolfi, Raffaella,Fusè, Marco,Zerla, Daniele,Cesarotti, Edoardo,Pellizzoni, Michela,Rimoldi, Isabella
, p. 3792 - 3800 (2015/05/20)
In this research work simple unsymmetrical 1,3-diamines were studied. The synthesis of the diamines started from non-commercial available compounds. S-5a and S,S-5c were obtained by biocatalysis with non conventional yeast, Rhodotorula rubra MIM 147, with
Catalytic asymmetric alkylation reactions for the construction of protected ethylene-amino and propylene-amino motifs attached to quaternary stereocentres
Moss, Thomas A.,Barber, David M.,Kyle, Andrew F.,Dixon, Darren J.
supporting information, p. 3071 - 3081 (2013/03/28)
An efficient catalytic and stereoselective method for the direct construction of protected ethylene-amino and propylene-amino scaffolds attached to quaternary stereocentres is reported. Preliminary investigations revealed a mild base catalysed nucleophilic ring opening of N-sulfonyl aziridines using the commercially available phosphazene base 2-tert-butylimino-2-diethylamino-1,3- dimethyl-perhydro-1,3,2-diazaphosphorine (BEMP) was possible and resulted in highly efficient alkylation reactions with a range of methine carbon acids. This reaction could be rendered highly asymmetric (up to 97 % ee) by employing phase-transfer catalysis to control stereoinduction. Incorporation of alkyl substituents onto the aziridine electrophile, resulted in a highly diastereoselective (up to 30:1 d.r.) variant of this methodology. A further extension using N-protected cyclic sulfamidates as the electrophilic component was successful with a range of pro-nucleophiles (up to 96 % ee and 45:1 d.r.) and allowed a range of nitrogen protecting groups (carbamate, sulfonyl, phosphonyl, benzyl) to be incorporated into the alkylation adducts. Finally, the utility of the products have been demonstrated in the synthesis of useful heterocycles and compounds bearing structural components of natural products. Open sesame: The enantio- and diastereoselective nucleophilic ring opening of protected aziridines and cyclic sulfamidates using asymmetric phase-transfer catalysis (PTC) is reported. The ring-opening alkylation reactions create quaternary chiral centres containing ethylene- and propylene-amino motifs in good yields with good to excellent enantioselectivities (see scheme). These reactions are broad in scope and a wide range of pro-nucleophiles are tolerated. Copyright
Catalytic enantio- and diastereoselective alkylations with cyclic sulfamidates
Moss, Thomas A.,Alonso, Beatriz,Fenwick, David R.,Dixon, Darren J.
supporting information; experimental part, p. 568 - 571 (2010/04/05)
(Figure Presented) Open for business: The enantio- and diastereoselective nucleophilic ring opening of five-membered and six-membered cyclic sulfamidates under asymmetric phase-transfer catalysis is presented. A range of pro-nucleophiles have been successfully alkylated in good yields and in good to excellent enantioselectivites.
Synthesis of enantiomerically pure γ-azidoalcohols by lipase-catalyzed transesterification
Kamal, Ahmed,Malik, M. Shaheer,Shaik, Ahmad Ali,Azeeza, Shaik
, p. 1078 - 1083 (2008/09/19)
An enantioselective synthesis of chiral γ-azidoalcohols via lipase-catalyzed resolution is described. The efficiency of various lipases and the effect of different solvents have been studied. Pseudomonas cepacia immobilized on diatomaceous earth (PS-D) in n-hexane catalyzed the transesterification process in an efficient manner providing γ-azidoalcohols in high enantiomeric excess.
Preparation of polymer-supported Ru-TsDPEN catalysts and use for enantioselective synthesis of (S)-fluoxetine
Li, Yangzhou,Li, Zhiming,Li, Feng,Wang, Quanrui,Tao, Fanggang
, p. 2513 - 2518 (2007/10/03)
Polymer-supported chiral ligands 9 and 17 were prepared based on Noyori's (1S,2S)- or (1R,2R)-N-(p-tolylsulfonyl)-1,2-diphenylethylenediamine. The combination with [RuCl2(p-cymene)]2 has been shown to exhibit high activities and enantioselectivities for heterogeneous asymmetric transfer hydrogenation of aromatic ketones (19a-c) with formic acid-triethylamine azeotrope as the hydrogen donor, whereby affording the respective optically active alcohols 20a-c, the key precursors of chiral fluoxetine. As exemplified by ligand 17 for substrate 19c, the catalysts can be recovered and reused in three consecutive runs with no significant decline in enantioselectivity. The procedure avoids the plausible contamination of fluoxetine by the toxic transition metal species. The Royal Society of Chemistry 2005.
The resolution of important pharmaceutical building blocks by palladium-catalyzed aerobic oxidation of secondary alcohols
Caspi, Daniel D.,Ebner, David C.,Bagdanoff, Jeffrey T.,Stoltz, Brian M.
, p. 185 - 189 (2007/10/03)
The palladium-catalyzed aerobic oxidative kinetic resolution of key pharmaceutical building blocks is described. Substrates investigated are relevant to the enantioselective preparation of Prozac, Singulair, and the promising hNK-1 receptor antagonist from Merck. The latter provides the most selective aerobic oxidative kinetic resolution yet described.
Process for the preparation of enantiomerically pure 3-phenyl-3-hydroxypropylamine
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Page 5, (2008/06/13)
The present invention relates to an improved process for the synthesis of enantiomerically pure 3-phenyl-3-hydroxypropylamine of formula I; more particularly the present invention relates to the said process using styrene; the synthetic strategy features a Sharpless asymmetric dihydroxylation (SAD) route to the target compound, using styrene, a readily accessible starting material gives the optically pure dihydroxy compound (ee >97%; the selective monotosylation of primary alcohol, nucleophilic displacement by cyano and subsequent reduction to amino group furnishes the desired 3-phenyl-3-hydroxypropylamine in enatiomerically pure form, a key intermediate in the synthesis of variety of oxetine related anti-depressant drugs.
[3H]-(R)-NPTS, a radioligand for the type 1 glycine transporter.
Lowe 3rd., John A,Drozda, Susan E,Fisher, Katherine,Strick, Christine,Lebel, Lorraine,Schmidt, Christopher,Hiller, Donna,Zandi, Kathleen S
, p. 1291 - 1292 (2007/10/03)
The synthesis of NPTS, 6, a potent inhibitor of the type 1 glycine transporter (GlyT1) is described, as well as preparation of 6 in optically active and tritiated form for use as a radioligand for affinity displacement assay of GlyT1.
Arylpropanolamines incorporating an antioxidant function as neuroprotective agents
Joubran, Lida,Jackson, W. Roy,Campi, Eva M.,Robinson, Andrea J.,Wells, Bradley A.,Godfrey, Peter D.,Callaway, Jennifer K.,Jarrott, Bevyn
, p. 597 - 605 (2007/10/03)
A series of arylpropanolamines containing dipyrrolidinylpyrimidines as an antioxidant function have been synthesized and evaluated as dual function neuroprotective agents. Their in vitro efficacy as sodium channel blocking agents and antioxidants has been evaluated and compared with those of the ethanolamine derivative (1), which has been shown to be neuroprotective in a rat model of stroke. The ability of the present compounds to displace 3H-BTX toxin from sodium-ion channels in a rat brain membrane fraction was shown to be largely independent of the substituents on the aryl ring, which suggests that this activity may be mainly associated with the aminopyrimidine moiety. Structure-activity relationships for antioxidant efficacy were less clear, but the unsymmetrical pyrimidines were consistently more active than their symmetrical isomers. A brief theoretical investigation of this observation is reported.