- Double asymmetric induction as method for the synthesis of chiral organophosphorus compounds
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New examples of multistereoselective syntheses of organophosphorus compounds are described.
- Kolodiazhnyi, Oleg I.
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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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- 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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- 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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scheme or table
p. 687 - 688
(2009/04/06)
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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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- 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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p. 1023 - 1026
(2007/10/03)
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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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- Asymmetric synthesis of α-substituted alkylphosphonates based on symmetrical dialkyl phosphites
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Chiral C2-symmetrical dialkyl phosphites and C3-symmetrical trialkyl phosphites, derived from (-)-borneol, (-)-menthol, and 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, were studied as the starting reagents for the preparation of chiral organophosphorus compounds. The reactions of C2-symmetrical dialkyl phosphites and C3-symmetrical trialkyl phosphites with aldehydes and amines or aldehydes are accompanied by asymmetrical induction at the α-carbon atom to yield optically active α-aminoalkylphosphonates or α-hydroxyalkylphosphonates, respectively. The stereoselectivity of the reaction depends on the structure of the starting compounds and the reaction conditions.
- Kolodiazhnyi,Grishkun,Sheiko,Demchuk,Thoennessen,Jones,Schmutzler
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p. 1568 - 1573
(2007/10/03)
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- Chiral symmetric phosphoric acid esters as sources of optically active organophosphorus compounds
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Chiral symmetric di- and trialkylphosphites, derivatives of (-)-borneol, (-)-menthol and (-)-1,2:5,6-di-Oisopropylidene-α-D-glucofuranose, were studied as starting reagents for the preparation of chiral organophosphorus compounds. The reaction occurs by a
- Kolodiazhnyi, Oleg I.,Grishkun, Evgen V.,Sheiko, Serge,Demchuk, Oleg,Thoennessen, Holger,Jones, Peter G.,Schmutzler, Reinhard
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p. 1645 - 1649
(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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- A Simple, Efficient Synthesis of Dibenzyl and Di-p-nitrobenzyl 1-Hydroxyalkanephosphonates
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Dibenzyl and di-p-nitrobenzyl 1-hydroxyalkanephosphonates 3a-i are prepared by alkylation of 1-hydroxyalkanephosphonic acids 1 with O-benzyl and O-(p-nitrobenzyl)-N,N'-dicyclohexylisoureas 2.
- Hoffmann, Maria
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