- New method for the asymmetric reduction of ketophosphonates
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Chiral reducing reactants were prepared from lithium, sodium, or tetrabutylammonium borohydrides and (S)- or (R)-tartaric acids. Copyright Taylor & Francis Group, LLC.
- Nesterov, Vitaly V.,Kolodiazhnyi, Oleg I.
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- New method for the asymmetric hydroboration of ketophosphonates and the synthesis of phospho-carnitine
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The reduction of α- or β-ketophosphonates with a chiral reactant 1, prepared from sodium borohydride and (R)- or (S)-tartaric acids, led to the formation of both (S)- and (R)-α- or β-hydroxyphosphonates in high yields. The stereoselectivity of the reactio
- Nesterov, Vitaly V.,Kolodiazhnyi, Oleg I.
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- Substrate-Based fragment identification for the development of selective, nonpeptidic inhibitors of striatal-enriched protein tyrosine phosphatase
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High levels of striatal-enriched protein tyrosine phosphatase (STEP) activity are observed in a number of neuropsychiatric disorders such as Alzheimer's disease. Overexpression of STEP results in the dephosphorylation and inactivation of many key neuronal
- Baguley, Tyler D.,Xu, Hai-Chao,Chatterjee, Manavi,Nairn, Angus C.,Lombroso, Paul J.,Ellman, Jonathan A.
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p. 7636 - 7650
(2013/11/06)
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- Enantioselective reduction of ketophosphonates using adducts of chiral natural acids with sodium borohydride
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A method for asymmetric reduction of α- and β-ketophosphonates using chiral complexes prepared from sodium borohydride and natural aminoacids or tartaric acids was developed. Reduction of α or β-ketophosphonates by these reagents led to formation of chiral (S)- or (R)- hydroxyphosphonates. Reduction of chiral di-(1R,2S,5R)-menthylketophosphonates by the chiral complexes NaBH4/(R,R)-proline or NaBH4/(R,R)-tartaric acid due to the double matched asymmetric induction resulted in increased stereoselectivity of the reaction and led to the formation of hydroxyphosphonates up to 90% ee or higher. Dimenthyl 2-hydroxy-3- chloropropylphosphonate was utilized as a chiron for the preparation of a number of biologically active compounds in multigram quantity. ARKAT-USA, Inc.
- Gryshkun,Nesterov,Kolodyazhnyi
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p. 100 - 117
(2013/09/24)
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- Catalytic enantioselective pudovik reaction of aldehydes and aldimines with tethered bis(8-quinolinato) (TBOx) aluminum complex
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New chiral tethered bis(8-quinolinolato) (TBOx) aluminum(III) complexes effectively catalyze the addition of phosphites to aldehydes and aldimines to give enantioenriched α-hydroxy and α-amino phosphonates in high yields and enantioselectivities with unpr
- Abell, Joshua P.,Yamamoto, Hisashi
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body text
p. 10521 - 10523
(2009/02/04)
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- Synthesis of optically active hydroxyphosphonates
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The reduction of dimenthyl ketophosphonates with sodium borohydride involves asymmetric induction at the a-carbon atom, resulting in a small excess of the (R)-enantiomer of the a-hydroxyphosphonate formed. A higher ee purity was achieved if the reduction
- Guliaiko, Irina,Nesterov, Vitaly,Sheiko, Sergei,Kolodiazhnyi, Oleg I.,Freytag, Matthias,Jones, Peter G.,Schmutzler, Reinhard
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p. 133 - 139
(2008/09/18)
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- Organic catalysis of phospha-aldol condensation
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Phospha-aldol reaction of dialkylphosphites with carbonyl compounds is catalyzed by cinchonine alkaloids and thier modified derivatives to give optically active hydroxyphosphonates. The use of diastereomeric pairs of alkaloids allowed obtaining both optic
- Kolodyazhnaya,Kukhar,Kolodyazhnyi
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scheme or table
p. 2043 - 2051
(2009/04/13)
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- Efficient method for the asymmetric reduction of α- and β-ketophosphonates
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An efficient and versatile method for the asymmetric reduction of α- and β-ketophosphonates using chiral reactant derived from sodium borohydride and l-(+)- or d-(-)-tartaric acid is developed. The methodology was used for the preparation of a number of biologically interesting enantiomerically pure products: including 2,3-epoxypropylphosphonate 11, 2-hydroxy-3-aminopropylphosphonic acid 14 (phospho-GABOB), phospho-carnitine 19, and others in multigram scale.
- Nesterov,Kolodiazhnyi
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p. 6720 - 6731
(2008/02/07)
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- Enantioselective reduction of ketophosphonates using chiral acid adducts with sodium borohydride
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A method for asymmetric reduction of α-and β-ketophosphonates using a chiral complex prepared from sodium borohydride and D-or L-tartaric acid is developed. Reduction of α-or β-ketophosphonates by these reagents led to formation of corresponding (S)-or (R
- Nesterov,Kolodyazhnyi
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p. 1022 - 1030
(2008/02/05)
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- Chiral, non-racemic α-hydroxyphosphonates and phosphonic acids via stereoselective hydroxylation of diallyl benzylphosphonates
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Chiral, non-racemic α-hydroxyphosphonates have been prepared in high enantiomeric excess (96-98% ee), via stereoselective oxaziridine-mediated hydroxylation of diallyl benzylphosphonates. The enantiomeric purity and absolute configuration of the α-hydroxy
- Skropeta, Danielle,Schmidt, Richard R.
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p. 265 - 273
(2007/10/03)
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- Reactions of Chiral Phosphorous Acid Diamides: The Asymmetric Synthesis of Chiral α-Hydroxy Phosphonamides, Phosphonates, and Phosphonic Acids
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Addition of aldehydes to the anions of chiral phosphorous acid diamides in THF solution gave α-hydroxy phosphonamides in good yield.The diastereoselectivity was strongly dependent upon the diamide used and ranged from poor to good.The phosphorous acid dia
- Blazis, Vincent J.,Koeller, Kevin J.,Spilling, Christopher D.
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p. 931 - 940
(2007/10/02)
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- Enzymes in Organic Chemistry, Part 1: Enantioselective Hydrolysis of α-(Acyloxy)phosphonates by Esterolytic Enzymes
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α-Hydroxyphosphonates (+/-)-3 were prepared and transformed into esters (+/-)-5.Eight lipases as well as pig liver esterase were tested as catalysts for enantioselective hydrolyses of α-(acyloxy)phosphonates in a biphasic system.Two of them proved to be useful.The highest enantioselectivity was obtained with lipase F-AP 15 and α-(acetyloxy)phenylmethylphosphonates (+/-)-5a and (+/-)-5b as substrates.The (S)-enantiomers were exclusively hydrolyzed to give optically pure alcohols (S)-(-)-3a and (S)-(-)-3b.Lipases AP 6 and F-AP 15 were used to prepare phosphonates(S)-(-)-3b, (S)-(+)-3d and (S)-(-)-3e on a preparative scale with an enantiomeric excess of 81percent, 87percent, and 89percent, respectively.The absolute configurations of the α-hydroxyphosphonates were assigned by Horeau's method and 1H NMR spectroscopy of Mosher's derivatives.
- Li, Yong-Fu,Hammerschmidt, Friedrich
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p. 109 - 120
(2007/10/02)
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