82101-87-9Relevant academic research and scientific papers
Novel cobalt(0)- or magnesium-mediated approaches to β-ketophosphonates
Orsini, Fulvia,Di Teodoro, Emanuela,Ferrari, Marinella
, p. 1683 - 1688 (2007/10/03)
Two novel approaches to β-ketophosphonates, based on cobalt(0)- or magnesium-mediated reactions of α-halophosphonates with esters are described.
SmI2-mediated reactions of diethyl iodomethylphosphonate with esters and lactones: A highly stereoselective synthesis of a precursor of the C-glycosyl analogue of thymidine 5′-(β-L-rhamnosyl)diphosphate
Orsini, Fulvia,Caselli, Alessandro
, p. 7259 - 7261 (2007/10/03)
In the presence of samarium iodide diethyl iodomethylphosphonate reacts with esters to afford β-ketophosphonates. The protocol has been applied to sugar lactones to afford in fairly good yields intermediates that are useful precursors for a variety of potentially bioactive compounds, such as the C-glycosyl analogue of thymidine 5′-(β-L-rhamnosyl)diphosphate.
Biocatalytic syntheses of chiral non-racemic 2-hydroxyalkanephosphonates
Zurawinski, Remigiusz,Nakamura, Kaoru,Drabowicz, Jozef,Kielbasinski, Piotr,Mikolajczyk, Marian
, p. 3139 - 3145 (2007/10/03)
A series of 2-oxoalkanephosphonates 2 were screened for reduction with Geotrichum candidum. Only diethyl 2-oxopropanephosphonate 2a underwent asymmetric reduction to give (+)-(R)-diethyl 2-hydroxypropanephosphonate 3a with 98% e.e. In turn, a series of racemic 2-hydroxyalkanephosphonates 3 were acetylated under kinetic resolution conditions in the presence of various lipases to give the corresponding 2-acetoxyalkanephosphonates 4 and recovered alcohols 3 in good yields and with e.e. up to 93%.
Preparation of 1-aminoalkylphosphonic acids and 2-aminoalkylphosphonic acids by reductive amination of oxoalkylphosphonates
Ryglowski, Artur,Kafarski, Pawel
, p. 10685 - 10692 (2007/10/03)
By reacting dialkyl 1-oxo- or 2-oxoalkylphosphonates with benzhydrylamine followed by reduction with triacetoxyborohydride and acid hydrolysis gave corresponding aminoalkylphosphonic acids with satisfactory yields. The use of benzylamine, α-methylbenzylamine and tritylamine was unsuccessful in the case of dialkyl 1-oxoalkylphosphonates whereas conversion of 2-oxoalkylphosphonates was also achieved although with lower yields.
REGIOCONTROLLED METALATION OF DIETYHL β-DIALKYLAMINOVINYLPHOSPHONATES: A NEW SYNTHESIS OF SUBSTITUTED β-KETOPHOSPHNATES
Boeckman, Robert K.,Walters, Michael A.,Koyano, Hiroshi
, p. 4787 - 4790 (2007/10/02)
The metalation of diethyl β-dialkylaminovinylphosphonates (vinylogous phosphoramides (VPA)) and their reaction with a variety of electrophiles is described.Upon mild hydrolysis these derivatives provide good yields of β-ketophosphonates.
