Organic catalysis of phospha-aldol condensation

Kolodyazhnaya, A. O.; Kukhar, V. P.; Kolodyazhnyi, O. I.

doi:10.1134/s1070363208110091

Cited by 11 publications

(9 citation statements)

References 22 publications

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“…Later on, Kolodiazhnyi et al demonstrated that diastereoselectivity of the reaction involving aromatic aldehydes and (−)- 56 could be improved by the addition of a catalytic amount of cinchonine alkaloids and its structure influenced the stereochemical direction of the reaction. 96 For instance, in the case of 2-nitrobenzaldehyde and the use of cinchonidine, the desired ( R )-α-hydroxyphosphonate 89d was obtained with de 75%. In turn, the application of quinine gave rise to ( S )-α-hydroxyphosphonate 89d .…”

Section: Application Of H–p Species Bearing Chiral Alcohol Attached T...mentioning

confidence: 99%

Asymmetric synthesis of organophosphorus compounds using H–P reagents derived from chiral alcohols

Gbubele

Olszewski

2021

Org. Biomol. Chem.

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Section: Application Of H–p Species Bearing Chiral Alcohol Attached T...mentioning

confidence: 99%

Asymmetric synthesis of organophosphorus compounds using H–P reagents derived from chiral alcohols

Gbubele

Olszewski

2021

Org. Biomol. Chem.

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“…The reaction was carried out in toluene or without a solvent in the presence of 20 mole percent of the alkaloid. The progress of the reaction was monitored by thin layer chromatography and 31 P NMR [29][30][31]. The reaction proceeded rather slowly, but with good yields of chiral hydroxyphosphonates.…”

Section: Diastereoselective Substitution Reactionsmentioning

confidence: 99%

Stereoselective Syntheses of Organophosphorus Compounds

Kolodiazhnyi,

Kolodiazhna

2024

Symmetry

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The review is devoted to the theoretical and synthetic aspects of the stereochemistry of organophosphorus compounds. Organophosphorus compounds are not only widely exist in biologically active pharmaceuticals and agrochemicals, but also have widespread applications in material science and organic synthesis as ligands for transition metal complexes. One of the mainstreams for the development in this field is the creation of biologically active organophosphorus compounds that are searched and used as drugs or plant-protecting agents, which leads to the elaboration of advanced methods and monitoring, yielding up-to-date approaches to perform synthesis in an environmentally friendly manner. The review consists of two parts. The first part presents methods for the asymmetric synthesis of organophosphorus compounds using asymmetric organocatalysis and metal complex catalysis. In the review is described the nature of the chirality generation in the prebiotic period, the mechanisms of asymmetric induction, and double stereodifferentiation are discussed. The use of these methods for the preparation of chiral phosphorus analogs of natural compounds (phosphono-isonorstatin, phosphono-GABOB, phosphacarnitine, bis-phosphonates, and others) is described. Some data concerning of λ5-phosphanediones as metaphosphate anion analogues are also reported. The second part of the presented review shows examples of the use of these methods for the synthesis of phosphorus analogues of natural compounds—chiral phosphonoamino acids and hydroxyphosphonates: phosphonoaspartic acid, phosphonoglutamic acid, phosphonohomoproline, chiral bis-phosphonates. The reaction of dehydration aromatization with the formation of pho sphono isoindolinones, including isoindolinone bis-phosphonates, has been studied. Some of the synthesized compounds showed biological activity as protein tyrosine phosphatase inhibitors. A phosphonic analogue of iso-norstatine was synthesized. A stereoselective method for the synthesis of tetradecapentaenoic acid derivatives was developed.

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“…α-Hydroxyphosphonic acids ( 42 ) were prepared by the hydrochloric acid-promoted hydrolysis of hydroxyphosphonates ( 41 ) ( Scheme 21 ) [ 96 ]. The hydrolysis was performed using 6 N HCl in dioxane-water at 80 °C for 3 days.…”

Section: Acidic Hydrolysis Of Phosphinates and Phosphonatesmentioning

confidence: 99%

The Hydrolysis of Phosphinates and Phosphonates: A Review

Harsági

Keglevich

2021

Molecules

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Phosphinic and phosphonic acids are useful intermediates and biologically active compounds which may be prepared from their esters, phosphinates and phosphonates, respectively, by hydrolysis or dealkylation. The hydrolysis may take place both under acidic and basic conditions, but the C-O bond may also be cleaved by trimethylsilyl halides. The hydrolysis of P-esters is a challenging task because, in most cases, the optimized reaction conditions have not yet been explored. Despite the importance of the hydrolysis of P-esters, this field has not yet been fully surveyed. In order to fill this gap, examples of acidic and alkaline hydrolysis, as well as the dealkylation of phosphinates and phosphonates, are summarized in this review.

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Organic catalysis of phospha-aldol condensation

Cited by 11 publications

References 22 publications

Asymmetric synthesis of organophosphorus compounds using H–P reagents derived from chiral alcohols

Asymmetric synthesis of organophosphorus compounds using H–P reagents derived from chiral alcohols

Stereoselective Syntheses of Organophosphorus Compounds

The Hydrolysis of Phosphinates and Phosphonates: A Review

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