Dyadic phosphorus-carbon tautomerism

Mastryukova, T. A.; Aladzheva, I. M.; Leont'eva, I. V.; Petrovski, P.V.; Fedin, É. I.; Кабачник, М. И.

doi:10.1351/pac198052040945

Cited by 24 publications

(8 citation statements)

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“…In most cases, phosphonates have been used as P-nucleophiles. It is known that a phosphonate-phosphite tautomerism exists with the phosphite form as the active nucleophilic species and the phosphonate tautomer as the almost exclusively favored but non-nucleophilic (resting) form 21,22 (Scheme 4).…”

Section: Catalytic Asymmetric Hydrophosphonylation Of Iminesmentioning

confidence: 99%

Catalytic asymmetric synthesis of α- and β-amino phosphonic acid derivatives

2006

Chem. Soc. Rev.

187

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Catalytic asymmetric reactions provide one of the most powerful and economical synthetic approaches to a variety of enantiomerically enriched compounds. As being analogues of the corresponding alpha- and beta-amino acids, optically active alpha- and beta-amino phosphonic acid derivatives have found widespread use in medicinal chemistry and the pharmaceutical sciences. Using catalytic amounts of chiral materials, asymmetric synthesis of enantiomerically enriched alpha- and beta-amino phosphonates has been a subject of growing interest. This tutorial review contains a compilation of the catalytic asymmetric synthetic methods developed to date and highlights their utility for obtaining these target compounds.

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Section: Catalytic Asymmetric Hydrophosphonylation Of Iminesmentioning

confidence: 99%

Catalytic asymmetric synthesis of α- and β-amino phosphonic acid derivatives

2006

Chem. Soc. Rev.

187

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“…Based on current investigation and the literature precedent, 13 a , e ,20,21 a plausible mechanism is proposed (Scheme 7). The diethyl phosphite ( T1 ) exists tautomerism with its known a phosphonate ( T2 ) species (Scheme 7i).…”

Section: Resultsmentioning

confidence: 99%

“…The diethyl phosphite ( T1 ) exists tautomerism with its known a phosphonate ( T2 ) species (Scheme 7i). 20 The active nucleophilic form ( T2 ) may react with molecular sulfur, producing an actual sulfur source ( T3 ) through a P–S bond under metal-free conditions. 21 The initial reaction between IP- 1a and sulfur source ( T3 ) is believed to furnish the pyridinium intermediate A through the SN Ar mechanism.…”

Section: Resultsmentioning

confidence: 99%

Diethyl phosphite-mediated switchable synthesis of bis(imidazoheterocycles) derived disulfanes and sulfanes using imidazoheterocycles and octasulfur

et al. 2022

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“…Moreover, catalytic enantioselective 1,2-addition to ketones has been limited in a few examples [37][38][39], unlike aldehydes and aldimines [40][41][42][43][44][45]. To overcome the difficulties in these undeveloped catalytic systems, catalysts must exhibit not only suitable Brønsted basicity to activate non-nucleophilic R 2 P(¼O)H (major, valence +V) into nucleophilic R 2 POH (minor, valence +III) [46,47], but also strong Brønsted or Lewis acidity to activate less-reactive substrates such as esters and ketones. …”

Section: Catalytic Enantioselective Addition Of Phosphorus Nucleophilmentioning

confidence: 99%

Brønsted Acid/Lewis Base Hybrid Complexes

Hatano

Ishihara

2015

Topics in Organometallic Chemistry

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Recent progress on our Brønsted acid/Lewis base hybrid complexes in some asymmetric catalyses is reviewed. Based on the rational design of conjugated acid-base catalysts, tailor-made supramolecular catalysts can show remarkable catalytic activity and higher-ordered selectivities that cannot be realized by ready-made single-molecule catalysts. The chiral supramolecular magnesium(II) binaphtholate complexes trigger the highly enantioselective 1,4-hydrophosphinylation and 1,2-hydrophosphonylation of α,β-unsaturated carbonyl compounds, direct Mannichtype reaction, and hetero-Diels-Alder reaction. Moreover, the advanced supramolecular catalysts are prepared in situ from chiral 3,3 0 -disubstituted binaphthols and biphenols, arylboronic acid, and B(C 6 F 5 ) 3 , for promoting the anomalous endo-/ exo-selective Diels-Alder reaction. The specific mechanism and deep insights into the possible key intermediates are discussed on the basis of rational design of chiral supramolecular Brønsted acid/Lewis base hybrid catalysts as artificial enzymes.

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Dyadic phosphorus-carbon tautomerism

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Cited by 24 publications

References 0 publications

Catalytic asymmetric synthesis of α- and β-amino phosphonic acid derivatives

Catalytic asymmetric synthesis of α- and β-amino phosphonic acid derivatives

Diethyl phosphite-mediated switchable synthesis of bis(imidazoheterocycles) derived disulfanes and sulfanes using imidazoheterocycles and octasulfur

Brønsted Acid/Lewis Base Hybrid Complexes

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