Journal ArticleDOI
Dimethyl 3-chloroprop-1-en-2-ylphosphonate. part 3. alkylation of anionic o and c nucleophiles and preparation of 1-alkenyl-2-phosphonates
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TLDR
In this paper, the Homer-Wittig reaction between formaldehyde and methylene diphosphonate is described for 2-phosphorylated 3-halopropenes.Abstract:
Under suitable reaction conditions 2-phosphorylated 3-chloropropene 1 monoalkylates methoxide, ethoxide, thiocyanate, methyl and ally1 Grignard reagents and acetamidomalonate—the latter reactions leading to 2-phosphorylated 1-butene, 1,5-hexadiene and C-alkylated α-aminoacids. Diethyl malonate and ethyl acetoacetate give mixtures of mono and dialkylated products whereas ethyl cyanoacetate gives only dialkylated product. Acetylacetone gives a dialkylated product - the monoalkylated intermediate undergoing acyl cleavage to give 2-phosphorylated 5-hexene-2-one as the major product. A new simple route for the preparation of 2-phosphorylated 3-halopropenes via a Homer-Wittig reaction between formaldehyde and methylene diphosphonate is described.read more
Citations
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Asymmetric Bioreduction of β‐Activated Vinylphosphonate Derivatives Using Ene‐Reductases
TL;DR: All active enzymes consistently furnished (R)-configurated products with exquisite stereoselectivity, thereby providing a stereo-complementary approach to current asymmetric hydrogenation protocols on similar compounds.
Journal ArticleDOI
Synthesis of β-aminovinylphosphonates by organocatalytic nucleophilic displacement of acetate with amines
TL;DR: In this article, the synthesis of diethyl β-aminovinylphosphonates from acetoxy phosphonate was described, which led to a series of functionalized title compounds in good to excellent yields.
Patent
Novel Inhibitors of Pyruvate Kinase as Therapeutic Agents for Cancer
TL;DR: In this paper, the present invention relates to compounds for the inhibition of pyruvate kinase and ATP production which are capable of inhibiting cancer cells proliferation, and it is shown that these compounds can be used for the treatment of cancer cells.
References
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Journal ArticleDOI
Addition of functionalized allylic bromides to terminal alkynes
Paul Knochel,J.F. Normant +1 more
TL;DR: In this paper, the authors propose to add zinc to terminal alkynes in the presence of zinc to give the highly functionnalized dienes, which are cyclized to various sex or seven membered carbo- or heterocycles.
Journal ArticleDOI
Exploration of N-phosphonoalkyl-, N-phosphonoalkenyl-, and N-(phosphonoalkyl)phenyl-spaced alpha-amino acids as competitive N-methyl-D-aspartic acid antagonists.
Christopher F. Bigge,Graham Johnson,Daniel F. Ortwine,James T. Drummond,Daniel Martin Retz,Laura J. Brahce,Linda L. Coughenour,Frank W. Marcoux,Albert W. Probert +8 more
TL;DR: Modeling studies suggest a folded conformation that brings the distal phosphonic acid group into close proximity with the alpha-carboxylate is required for binding, and Affinity decreased for analogues with alpha-carbon substitution, presumably because thealpha-substituent inhibits the folding of these structures into a bioactive conformation and occupies receptor-excluded volume.
Journal ArticleDOI
Synthèse de diènes-1,4 fonctionnalisés par addition de zinciques allyliques fonctionnalisés sur des alcynes vrais et leur cyclisation en hétérocycles ou carbocycles
P. Knochel,J.F. Normant +1 more
TL;DR: The addition of functionalized allylic bromides to terminal alkynes in the presence of zinc furnishes a great variety of highly functionalized 1,4-dienes with moderate to good yields as mentioned in this paper.
Journal ArticleDOI
“α-Methylene-γ-phostones”1 (5,5-di- and 5-monoalkyl-2-methoxy-3-methylene-1,2-oxaphospholan-2-ones). A phosphorus analog of the one-step reformatsky synthesis of α-methylene-γ-butyrolactones from ketones and aldehydes
Jean-Noël Collard,Claude Benezra +1 more
TL;DR: The first synthesis of α-methylene-γ-phostones (propylphostonates) using dimethyl bromo-3-propen-2 ylphosphonate and ketones and aldehydes, in the presence of zinc, is described in this paper.
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