Ring opening of epoxides with C-nucleophiles

Faiz, Sadia; Zahoor, Ameer Fawad

doi:10.1007/s11030-016-9686-7

Cited by 27 publications

(10 citation statements)

References 38 publications

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“…[ 24,25 ] Besides, the aminoglycosides can also be used as monomers to synthesize hyperbranched polymers via Michael‐addition reactions [ 26 ] of the primary amine groups. [ 27,28 ] The amino groups could also perform ring opening reactions with epoxides, [ 29,30 ] affording various lipid‐modified aminoglycosides and hyperbranched aminoglycosides. [ 31,32 ]…”

Section: Aminoglycosides As Building Blocks To Design Functional Biomaterialsmentioning

confidence: 99%

Aminoglycoside‐Based Biomaterials: From Material Design to Antibacterial and Gene Delivery Applications

Yang

Cheng

et al. 2021

Adv Funct Materials

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Aminoglycosides are a family of naturally isolated or chemically semi‐synthesized antibiotics consisting of aminocyclitols with several amino and saccharide units. The unique molecule structures render aminoglycosides promising building blocks with high reactivity to perform various non‐covalent and covalent reactions, and they are further employed to rationally fabricate versatile materials, such as hydrogels, amphiphiles, hyperbranched polymers, biointerfaces, and nanoparticles. Despite aminoglycosides are widely used in clinics to treat bacterial infections, almost all the efforts are focused on molecular modifications to reduce their toxicities and overcome antibiotic resistance, while their actions as building blocks to construct biomaterials are scarcely discussed. In this feature article, the current progress on the rational design, emergent properties, and promising biological applications of aminoglycoside‐based biomaterials are summarized. It is believed that this paper may provide guidance to develop new biomaterials using natural functional molecules as building blocks, and start a new life of aminoglycosides from the view of materials science.

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Section: Aminoglycosides As Building Blocks To Design Functional Biomaterialsmentioning

confidence: 99%

Aminoglycoside‐Based Biomaterials: From Material Design to Antibacterial and Gene Delivery Applications

Yang

Cheng

et al. 2021

Adv Funct Materials

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“…We envisioned that the presence of the Lewis basic oxygen and an adjacent electrophilic carbon atom may react with boroles in a way similar to that of the aforementioned 1,3-dipoles to provide a facile route to eight-membered BOC 6 rings. To our surprise, three discrete products were obtained, depending on the substitution on the epoxide, none of which are polymeric species, the typical products observed upon the addition of a Lewis acid to epoxides. − The chemistry described herein demonstrates the diverse reactivity of epoxides with pentaphenylborole.…”

Section: Introductionmentioning

confidence: 99%

Ring Opening of Epoxides Induced by Pentaphenylborole

et al. 2017

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The unsaturated antiaromatic BC 4 heterocycle pentaphenylborole has been shown to have diverse reactivity with a variety of substrates, including the insertion of polar functional groups into the ring as a route to conjugated boracycles. This work investigates the reactivity of a selection of epoxides with pentaphenylborole, both computationally and experimentally, revealing that the substitution is highly influential on the reaction outcome. Specifically, isobutylene oxide results in protodeborylation to a borabutadiene chain attributed to the acidic β-hydrogen atoms, 1,1-diphenylethylene oxide inserts the C 2 O unit to furnish a BOC 6 heterocycle, and cyclohexene oxide inserts two epoxides to form an unusual BC 8 O 2 ring. The last two species represent rare boroncontaining rings of eight atoms or greater, with the 11-membered species being only the second reported and the first crystallographically characterized.

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“…On the basis of a combination of reactivity and synthetic application of oxiranes in organic synthesis (Parker and Isaacs, 1959;Ready and Jacobsen, 2002;Azoulay et al, 2005;Wu and Xia, 2005;Padwaa and Murphree, 2006;Fustero et al, 2011;Singh et al, 2013;Zhao and Weix, 2014;Faiz and Zahoor, 2016), we decided to apply those three-membered heterocycles toward aminophosphonates. Recently we developed the method FIGURE 2 | Structures of (R)-β-hydroxy-γ -aminobutanoic acid (L-GABOB) and its organophosphorus analogs P-GABOB.…”

Section: Introductionmentioning

confidence: 99%

“…On the basis of a combination of reactivity and synthetic application of oxiranes in organic synthesis (Parker and Isaacs, 1959 ; Ready and Jacobsen, 2002 ; Azoulay et al, 2005 ; Wu and Xia, 2005 ; Padwaa and Murphree, 2006 ; Fustero et al, 2011 ; Singh et al, 2013 ; Zhao and Weix, 2014 ; Faiz and Zahoor, 2016 ), we decided to apply those three-membered heterocycles toward aminophosphonates. Recently we developed the method for the synthesis of two types of monofluorinated α, β-epoxyphosphonates with the vicinal and geminal arrangement of fluorine and phosphorus atoms via a Michaelis-Becker addition or by an intramolecular ring closure reaction (Rapp et al, 2015 ).…”

Section: Introductionmentioning

confidence: 99%

Highly Diastereoselective Construction of Carbon– Heteroatom Quaternary Stereogenic Centers in the Synthesis of Analogs of Bioactive Compounds: From Monofluorinated Epoxyalkylphosphonates to α-Fluoro-, β-, or γ-Amino Alcohol Derivatives of Alkylphosphonates

et al. 2021

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The synthesis of the stable surrogates of an important amino acid (R)-4-amino-3-hydroxybutyric acid (GABOB) such as substituted hydroxy aminophosphonic acids bearing a quaternary stereogenic center is presented. Highly diastereoselective formations of fluorinated spiroepoxy alkylphosphonate or related tertiary carbon-containing oxiranes from β-keto phosphonates possessing methyl, phenyl, or cyclohexenyl substituents, are reported. Stereoselective acid-promoted epoxide opening by bromide or azide followed by reduction/protection afforded tertiary bromides or N-Boc derivatives of β-amino-γ-hydroxy alkylphosphonates in most cases, while the reactions of oxiranes with different amines yielded their β-hydroxy-γ-amino regioisomers. Surprisingly, during the synthesis of amino phosphonic acids, we observe that the acid-induced rearrangement proceeded in a high diastereospecific manner, leading finally to substituted β-hydroxy-γ-aminoalkylphosphonic acids.

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Ring opening of epoxides with C-nucleophiles

Cited by 27 publications

References 38 publications

Aminoglycoside‐Based Biomaterials: From Material Design to Antibacterial and Gene Delivery Applications

Aminoglycoside‐Based Biomaterials: From Material Design to Antibacterial and Gene Delivery Applications

Ring Opening of Epoxides Induced by Pentaphenylborole

Highly Diastereoselective Construction of Carbon– Heteroatom Quaternary Stereogenic Centers in the Synthesis of Analogs of Bioactive Compounds: From Monofluorinated Epoxyalkylphosphonates to α-Fluoro-, β-, or γ-Amino Alcohol Derivatives of Alkylphosphonates

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