Reactions of Chiral Phosphorous Acid Diamides: The Asymmetric Synthesis of Chiral .alpha.-Hydroxy Phosphonamides, Phosphonates, and Phosphonic Acids

1995 ◽  
Vol 60 (4) ◽  
pp. 931-940 ◽  
Author(s):  
Vincent J. Blazis ◽  
Kevin J. Koeller ◽  
Christopher D. Spilling
Keyword(s):  
Asymmetric Synthesis ◽  
Phosphorous Acid ◽  
Phosphonic Acids

An efficient asymmetric synthesis of azetidine 2-phosphonic acids

2002 ◽  
Vol 43 (26) ◽  
pp. 4633-4636 ◽  
Author(s):  
Claude Agami ◽  
François Couty ◽  
Nicolas Rabasso
Keyword(s):  
Asymmetric Synthesis ◽  
Phosphonic Acids

scholarly journals Phosphonic acid: preparation and applications

2017 ◽  
Vol 13 ◽  
pp. 2186-2213 ◽  
Author(s):  
Charlotte M Sevrain ◽  
Mathieu Berchel ◽  
Hélène Couthon ◽  
Paul-Alain Jaffrès
Keyword(s):  
Phosphonic Acid ◽  
Functional Group ◽  
Phosphinic Acid ◽  
Phosphorous Acid ◽  
Direct Methods ◽  
Phosphonic Acids ◽  
Research Fields ◽  
Dialkyl Phosphonates ◽  
Review Reports ◽  
Acid Functional Group

The phosphonic acid functional group, which is characterized by a phosphorus atom bonded to three oxygen atoms (two hydroxy groups and one P=O double bond) and one carbon atom, is employed for many applications due to its structural analogy with the phosphate moiety or to its coordination or supramolecular properties. Phosphonic acids were used for their bioactive properties (drug, pro-drug), for bone targeting, for the design of supramolecular or hybrid materials, for the functionalization of surfaces, for analytical purposes, for medical imaging or as phosphoantigen. These applications are covering a large panel of research fields including chemistry, biology and physics thus making the synthesis of phosphonic acids a determinant question for numerous research projects. This review gives, first, an overview of the different fields of application of phosphonic acids that are illustrated with studies mainly selected over the last 20 years. Further, this review reports the different methods that can be used for the synthesis of phosphonic acids from dialkyl or diaryl phosphonate, from dichlorophosphine or dichlorophosphine oxide, from phosphonodiamide, or by oxidation of phosphinic acid. Direct methods that make use of phosphorous acid (H3PO3) and that produce a phosphonic acid functional group simultaneously to the formation of the P–C bond, are also surveyed. Among all these methods, the dealkylation of dialkyl phosphonates under either acidic conditions (HCl) or using the McKenna procedure (a two-step reaction that makes use of bromotrimethylsilane followed by methanolysis) constitute the best methods to prepare phosphonic acids.

ChemInform Abstract: An Efficient Asymmetric Synthesis of Azetidine 2-Phosphonic Acids.

ChemInform ◽  
2010 ◽  
Vol 33 (40) ◽  
pp. no-no
Author(s):  
Claude Agami ◽  
Francois Couty ◽  
Nicolas Rabasso
Keyword(s):  
Asymmetric Synthesis ◽  
Phosphonic Acids
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