900537-05-5Relevant academic research and scientific papers
Enantioselective reduction of ketophosphonates using adducts of chiral natural acids with sodium borohydride
Gryshkun,Nesterov,Kolodyazhnyi
, p. 100 - 117 (2013/09/24)
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.
New methods and strategies for asymmetric synthesis of organophosphorus compounds
Kolodiazhnyi,Guliayko,Gryshkun,Kolodiazhna,Nesterov,Kachkovskyi
scheme or table, p. 393 - 398 (2009/04/04)
New methods for the asymmetric synthesis of organophosphorus compounds were developed and applied for the preparation of a number of biologically important enantiomerically pure products. Copyright Taylor & Francis Group, LLC.
Efficient method for the asymmetric reduction of α- and β-ketophosphonates
Nesterov,Kolodiazhnyi
, p. 6720 - 6731 (2008/02/07)
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.
Di(1R,2S,5R)-menthyl 2-hydroxy-3-chloropropylphosphonate as a useful chiral synthon for the preparation of enantiomerically pure phosphonic acids
Nesterov, Vitaly V.,Kolodiazhnyi, Oleg I.
, p. 2400 - 2404 (2008/03/27)
Stereochemically pure di(1R,2S,5R)-menthyl (S)- and (R)-2-hydroxy-3- chloropropylphosphonates were synthesized by reaction of di(1R,2S,5R)-menthyl ketophosphonate with chiral complexes prepared from sodium borohydride and (R,R)-(+)-tartaric acid or with (
New method for the asymmetric hydroboration of ketophosphonates and the synthesis of phospho-carnitine
Nesterov, Vitaly V.,Kolodiazhnyi, Oleg I.
, p. 1023 - 1026 (2007/10/03)
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
