Carbohydrates in asymmetric synthesis: enantioselective allylation of aldehydes

Appelt, Helmoz R.; Limberger, Jane Beatriz; Weber, Minéia; Rodrigues, Oscar E. D.; Oliveira, Julieta Saldanha de; Lüdtke, Diogo S.; Braga, Antônio L.

doi:10.1016/j.tetlet.2008.05.109

Cited by 18 publications

(10 citation statements)

References 19 publications

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“…Recently, carbohydrates and their derivatives have emerged as an important tool for selective synthesis and as a chiral pool for the design of chiral ligands. They are used as chiral building blocks, precursors for drug synthesis and chiral catalysts in asymmetric catalysis (Dieguez et al, 2004a(Dieguez et al, , 2004b(Dieguez et al, , 2007Woodward et al, 2010;Boysen, 2007;Appelt et al, 2008). Despite the importance of carbohydrates in biological events, the pace of development of carbohydrate based therapeutics has been relatively slow.…”

Section: Resultsmentioning

confidence: 99%

Acylation of D-Glucose Derivatives over C5H5N: Spectral Characterization and in vitro Antibacterial Activities

Kawsar¹,

Uddin²,

Manchur³

et al. 2015

International J. of Biological Chemistry

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Methyl α-D-glucopyranoside was easily prepared by the treatment of D-glucose with anhydrous methyl alcohol in presence of hydrogen chloride at freezing temperature in good yield. Then N-acetylsulfanilylation of methyl α-D-glucopyranoside has been carried out by the direct method and afforded the 6-O-N-acetylsulfanilyl derivative in an excellent yield. In order to obtain newer products, the 6-O-N-acetylsulfanilyl derivative was further transformed to a series of 2,3,4-tri-O-acyl derivatives containing a wide variety of functionalities in a single molecular framework. The chemical structures of the newly synthesized compounds were elucidated by Fourier Transform Infrared spectroscopy (FTIR), 1 H-NMR (Proton nuclear magnetic resonance) spectroscopy elemental and physicochemical properties analysis. All the newly synthesized D-glucose derivatives were tested for their in vitro antibacterial activity against some human pathogenic bacterial strains. The study revealed that a good number of acylated products exhibited promising antibacterial activities. It is expected that the acylated derivatives of D-glucose may be considered as a potential source for developing new and better antibacterial agents against a number of pathogenic organism.

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Section: Resultsmentioning

confidence: 99%

Acylation of D-Glucose Derivatives over C5H5N: Spectral Characterization and in vitro Antibacterial Activities

Kawsar¹,

Uddin²,

Manchur³

et al. 2015

International J. of Biological Chemistry

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“…For racemic allylation variants, organozinc compounds are regularly used, because they are easily prepared from the corresponding allylic halides and zinc dust 6 and show a high tolerance towards a variety of functional groups. 7 To date, reports on the asymmetric Zn 2+ -mediated Barbier-type allylation reaction are scarce, 8 although high diastereoselectivity can be induced regarding the syn : anti ratio of the two chiral centers formed during the allylation with butyrolactone 4 (Scheme 1 ). 3 A possible explanation for the lack of asymmetric protocols may be that most reactions are run in highly coordinating and/or polar solvents (such as THF, DMF, DME or even water) which is essential for metal insertion into the carbon-halide bond.…”

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confidence: 99%

Asymmetric Synthesis of β‐Substituted α‐Methylenebutyro‐ lactones via TRIP‐Catalyzed Allylation: Mechanistic Studies and Application to the Synthesis of (S)‐(−)‐Hydroxymatairesinol

et al. 2013

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Asymmetric allylation of (hetero)aromatic aldehydes by a zinc(II)-allylbutyrolactone species catalyzed by a chiral BINOL-type phosphoric acid gave β-substituted α-methylenebutyrolactones in 68 to >99% ee and 52–91% isolated yield. DFT studies on the intermediate Zn2+-complex – crucial for chiral induction – suggest a six-membered ring intermediate, which allows the phosphoric acid moiety to activate the aldehyde. The methodology was applied to the synthesis of the antitumour natural product (S)-(−)-hydroxymatairesinol.

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“…All the products (3-6, 8-11) have been tested either pure or in solutions in several reactions. Among them: the addition of 4-hydroxycoumarin to enals, 38 allylation of aldehydes, 39 reduction of acetophenones with NaBH 4 . 28 Although we had fast and efficient conversions, our hybrid CD derivatives did not induce enantioselectivity.…”

Section: Uses and Applicationsmentioning

confidence: 99%

A new class of cationic cyclodextrins: synthesis and chemico-physical properties

et al. 2010

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A new class of positively charged triazole-bridged b-cyclodextrin (b-CD) derivatives have been synthesized in excellent yields (over 70%) through a copper-catalyzed azide-alkyne cycloaddition (CuAAC), starting from 6 I -azido-6 I -deoxy-b-CD or its permethylated derivative and a series of 1-butyl-3-alkynylimidazolium salts. The regioselective azide/alkyne [3 + 2] cycloaddition was efficiently carried out using metallic copper as the catalyst, affording very clean products. Easy access to such hybrid molecules that combine the properties of CDs and ionic liquids, may pave the way to a number of new applications in analytical chemistry and catalysis.

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Carbohydrates in asymmetric synthesis: enantioselective allylation of aldehydes

Cited by 18 publications

References 19 publications

Acylation of D-Glucose Derivatives over C5H5N: Spectral Characterization and in vitro Antibacterial Activities

Acylation of D-Glucose Derivatives over C5H5N: Spectral Characterization and in vitro Antibacterial Activities

Asymmetric Synthesis of β‐Substituted α‐Methylenebutyro‐ lactones via TRIP‐Catalyzed Allylation: Mechanistic Studies and Application to the Synthesis of (S)‐(−)‐Hydroxymatairesinol

A new class of cationic cyclodextrins: synthesis and chemico-physical properties

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