Preparation of phosphinic acids: Michael additions of phosphonous acids/esters to conjugated systems.

“…Phosphonite 1 smoothly reacts with trimethylsilyl acrylate in methylene chloride via 1,4-addition involving the POSi fragment to form corresponding ketene bis(trimethylsilyl) acetal 12 in high yield (cf. [11]), and treatment of acetal 12 with diethyl phosphite yields phosphinate 13 with two propionate fragments (Eq. (5)).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of new organophosphorus‐substituted derivatives of functionalized propionates and their analogues

Prishchenko

Ливанцов

Novikova

et al. 2008

Heteroatom Chemistry

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“…Arylphosphonous acids 8 and esters 6 can undergo addition reactions with aldehydes, imines and isocyanates to yield α-functionalised phosphinic acids and esters [13,14]. Thus, the intermediates 6 and 8 were silylated with trimethylchlorosilane and triethylamine in methylene chloride to yield a tri-valent phosphorus species, which underwent the addition reaction under mild conditions (room temperature) and in high yields.…”

Section: Methodsmentioning

confidence: 99%

Solid Supported Synthesis of Phosphinates Via Palladium (0) Catalysed Coupling Reactions

Haaf

2005

CCHTS

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In order to gain a broad access to phosphinic acid derivatives, a palladium catalysed coupling reaction of aryl iodides with hypophosphorous acid derivatives has been developed on the solid phase. The resulting arylphosphorous acids (or esters) were derivatised using addition reactions with aldehydes, imines and isocyanates, to give phosphinic acids (or esters) with alpha-hydroxy, alpha-amino or aminoacyl groups attached to the aryl phosphorus moiety. This approach provided a broad chemical entry into a class of polar phosphinates compounds which were rather difficult to handle using normal solution phase synthesis. The synthetic potential of this solid phase based methodology was demonstrated by the synthesis of targeted libraries against the enzyme dihydrodipicolinate synthase (DHDPS).

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“…The H -phosphinic component requires activation to the tervalent nucleophilic ester form, typically accomplished by silylation ( Scheme 2 ). Alternatively, the effect can be achieved by heating with hexamethyldisilazane (HMDS), by action of N,O -bis(trimethylsilyl)acetamide (BSA), or in the presence of chlorotrimethylsilane (TMSCl) and a tertiary amine [ 21 , 25 , 26 , 27 , 28 , 29 , 30 ]. After addition to an acrylate, the silylated adduct is decomposed with an alcohol or water.…”

Section: Synthesis Of the Phosphinic αα'-Dipeptide Backbonementioning

confidence: 99%

Synthesis and Modifications of Phosphinic Dipeptide Analogues

Mucha

2012

Molecules

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Pseudopeptides containing the phosphinate moiety (-P(O)(OH)CH2-) have been studied extensively, mainly as transition state analogue inhibitors of metalloproteases. The key synthetic aspect of their chemistry is construction of phosphinic dipeptide derivatives bearing appropriate side-chain substituents. Typically, this synthesis involves a multistep preparation of two individual building blocks, which are combined in the final step. As this methodology does not allow simple variation of the side-chain structure, many efforts have been dedicated to the development of alternative approaches. Recent achievements in this field are summarized in this review. Improved methods for the formation of the phosphinic peptide backbone, including stereoselective and multicomponent reactions, are presented. Parallel modifications leading to the structurally diversified substituents are also described. Finally, selected examples of the biomedical applications of the title compounds are given.

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Preparation of phosphinic acids: Michael additions of phosphonous acids/esters to conjugated systems.

Cited by 52 publications

References 1 publication

Synthesis of new organophosphorus‐substituted derivatives of functionalized propionates and their analogues

Synthesis of new organophosphorus‐substituted derivatives of functionalized propionates and their analogues

Solid Supported Synthesis of Phosphinates Via Palladium (0) Catalysed Coupling Reactions

Synthesis and Modifications of Phosphinic Dipeptide Analogues

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