Solid-phase synthesis of α-hydroxy phosphonates and hydroxystatine amides. Transition-state isosteres derived from resin-bound amino acid aldehydes

Dolle, Roland E.; Herpin, Timothy F.; Shimshock, Yvonne Class

doi:10.1016/s0040-4039(01)00097-1

Cited by 26 publications

(13 citation statements)

References 11 publications

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“…We focused on the Pudovik‐type reaction of aldehydes, which involves the addition of dialkylphosphites to carbonyl compounds to generate α‐hydroxyphosphonates and is a powerful and direct means of forming CP bonds. To date, a variety of catalysts have been applied to this reaction, including cesium fluoride,12 triethylamine,13 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU)14 and lithium diisopropylamide (LDA),15 as well as BF 3 ⋅ OEt 2 ,16 TMSCl,17 and trifluoroacetic acid (TFA) 18. We therefore began by surveying suitable catalysts for a one‐pot phosphinate Passerini/Pudovik reaction aimed at obtaining the relatively stable α‐hydroxyphosphinate derivatives.…”

Section: Resultsmentioning

confidence: 99%

“…Since we had already found that the a-(phosphinyloxy)amides are relatively unstable during silica gel column chromatography, the conversion of 4 to more stable compounds would have an additional practical advantage. We focused on the Pudovik-type reaction of aldehydes, which involves the addition of dialkylphosphites to carbonyl [a] Ph (3 a) C H 2 Cl 2 4 9 4( 4 aaa) -7 [b] Ph (3 a [12] triethylamine, [13] 1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU) [14] and lithium diisopropylamide (LDA), [15] as well as BF 3 ·OEt 2 , [16] TMSCl, [17] and trifluoroacetic acid (TFA). [18] We therefore began by surveying suitable catalysts for a one-pot phosphinate Passerini/Pudovik reaction aimed at obtaining the relatively stable a-hydroxyphosphinate derivatives.…”

Section: Resultsmentioning

confidence: 99%

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A One‐Pot O‐Phosphinative Passerini/Pudovik Reaction: Efficient Synthesis of Highly Functionalized α‐(Phosphinyloxy)amide Derivatives

Soeta

Matsuzaki

Ukaji

2014

Chemistry A European J

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A one-pot O-phosphinative Passerini/Pudovik reaction has been developed, based on reacting aldehydes, isocyanides, and phosphinic acids followed by the addition of second aldehydes to form the corresponding α-(phosphinyloxy)amide derivatives. This is the first reported instance of a Passerini-type, isocyanide-based multicomponent reaction using a phosphinic acid instead of a carboxylic acid. The nucleophilicity of the phosphinate group allows a subsequent catalytic Pudovik-type reaction, affording the highly functionalized α-(phosphinyloxy)amide derivative in high yield. A wide range of aldehydes and isocyanides are applicable to this reaction.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

A One‐Pot O‐Phosphinative Passerini/Pudovik Reaction: Efficient Synthesis of Highly Functionalized α‐(Phosphinyloxy)amide Derivatives

Soeta

Matsuzaki

Ukaji

2014

Chemistry A European J

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“…The stereoselectivity of this process is dependent on the reaction conditions and the nature of the solvent and base. Solid-phase synthesis of b-amino-ahydroxyphosphonates using of resin-bound chiral N-acylated aminoaldehydes has also been reported [184]. When chiral keto-phosphonates of the type 97 derived from naturally occurring 1-amino acids were introduced into the reaction, 2-amino-1-hydroxy-alkane-1,1-bisphosphonic acids 98 were prepared in moderate yields [185].…”

Section: Synthesis Of B-aminophosphonates J213mentioning

confidence: 98%

Chemistry of Aminophosphonic Acids and Phosphonopeptides

Kukhar

Romanenko

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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Aminophosphonic (and aminophosphinic) acids occupy a prominent position in the understanding of bioprocesses in living organisms and in the construction of new bioregulators -pharmaceuticals and agrochemicals. The so-called phosphorus analogs of the amino acids, aminophosphonic and aminophosphinic acids, are amino acid mimetics in which the carboxylic group is substituted by a phosphonic acid residue P(O)(OH) 2 or phosphinic acid group P(O)(OH)R. The replacement of the carboxylic group by a phosphonic or related moiety results in a number of important consequences: the central atom of a phosphonic acid function consists of an additional substituent that has a tetrahedral configuration in contrast to the planar carbonyl atom of carboxylic group. There are also significant differences in the acidity and steric bulk of these residues. The tetrahedral configuration of the pentavalent phosphorus atom mimics the transition state of the peptide bond cleavage reaction in some enzyme-substrate interactions that is used in the synthesis of new inhibitors. The hydrolytic stability of CÀP bonds is often used in order to prepare stable analogs of bioactive phosphates OÀP(O)(OH) 2 . In addition, aminophosphonic acids and their derivatives are important as metal-complexing agents, which have diagnostic and therapeutic applications, and as industrial chemicals in water treatment, metal extraction, or pollution control.Synthesis, and the chemical, physical, and biological properties of aminophosphonic acids and some directions for their practical application are presented in a number of reviews and book chapters. The most comprehensive account of the chemistry and biology of aminophosphonates and aminophosphinate which covers literature up to 2000 is presented in Kukhar and Hudson ([1] and references therein). Readers are referred to this reference for more detailed information concerning specific aspects of the chemistry and biological activity of aminophosphonic acid derivatives. The purpose of this chapter is to give an updated report on aminophosphonic acids as analogs of amino acids. Numerous heterocyclic compounds that contain both phosphonic and amino groups will not be covered in this report.

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“…26 Solid-phase synthesis of b-amino-a-hydroxy phosphonates 34-38 by hydrophosphinylation of resin-bound N-acylated amino aldehydes 32 has recently been reported. 27 Treatment of resin-bound aldehyde 32 with dimethyl phosphite using Et 3 N as base followed by photolysis furnished the a-hydroxy dimethyl phosphonates 34 as a 1 : 1 mixture of diastereoisomers. A survey of the reaction of other amino acid aldehydes (e.g., alanine, leucine, substituted phenylalanine acylated with electron-rich/deficient aroyls, heteroaroyls, substituted acyls) with commercially available dialkyl and dibenzyl phosphites gave similarly clean conversions to b-amino-a-hydroxy phosphonates 35-38 with diastereomeric ratios ranging from 1 : 1 to 3 : 1 (Scheme 13.7).…”

Section: Several Literature Reportsmentioning

confidence: 99%

Asymmetric Synthesis of α-Substituted-β-Amino Phosphonates and Phosphinates and β-Amino Sulfur Analogs

Palacios¹,

Alonso²,

Santos³

2005

Enantioselective Synthesis of Β-Amino Acids

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Solid-phase synthesis of α-hydroxy phosphonates and hydroxystatine amides. Transition-state isosteres derived from resin-bound amino acid aldehydes

Cited by 26 publications

References 11 publications

A One‐Pot O‐Phosphinative Passerini/Pudovik Reaction: Efficient Synthesis of Highly Functionalized α‐(Phosphinyloxy)amide Derivatives

A One‐Pot O‐Phosphinative Passerini/Pudovik Reaction: Efficient Synthesis of Highly Functionalized α‐(Phosphinyloxy)amide Derivatives

Chemistry of Aminophosphonic Acids and Phosphonopeptides

Asymmetric Synthesis of α-Substituted-β-Amino Phosphonates and Phosphinates and β-Amino Sulfur Analogs

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