β-Cyclodextrin as an efficient catalyst for the one-pot synthesis of 1-aminophosphonic esters in water

Kaboudin, Babak; Sorbiun, Mina

doi:10.1016/j.tetlet.2007.10.082

Cited by 61 publications

(17 citation statements)

References 59 publications

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“…However, α -aminophosphonic esters were obtained in a one -pot synthesis with β -CD (45 -82%) with good purity under mild conditions by the reaction of diethyl phosphate with a mixture of aldehyde and amine at refl ux for 12 -24 h (Figure 4.14 ). 56 The Strecker reaction that is the nucleophilic addition of trimethylsilyl cyanide (TMSCN) to imines in water has been developed in the presence of β -CD to afford α -aminonitriles ( Figure 4.15 a). 57 The use of CD precludes the use of either acid or base, and the catalyst can be recycled a number of times without loss in activity.…”

Section: Additionmentioning

confidence: 99%

Reactions Mediated by Cyclodextrins

Takahashi

2010

Molecular Encapsulation

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IntroductionCyclodextrins (CDs) are naturally occurring torus -shaped molecules composed of 6, 7, or 8 D -glucose units. A fascinating property of CDs is their ability to incorporate other organic compounds into their cavities in aqueous solution. 1 Since their discovery, CDs have served as prototypes for novel host compounds and catalysts. The use of CDs as microvessels to perform chemical reactions has attracted the interest of chemists since the 1960s. 2 Effects of CDs on reactions are mainly divided into two categories. The fi rst effect is the catalytic effect, designated as the ' enzyme model. ' CD and the reactant initially form a CD -reactant reaction intermediate involving a covalent bond, which then proceeds to product. The second effect does not involve a covalent bond. The cavity of CD presents a new reaction environment to the reactant, an ' extra reaction fi eld ' , in which the reactivity, such as rate or selectivity, changes. In these cases, the role of the CD does not always catalyze, but mediates the reaction. The CD cavity is less polar than the bulk aqueous medium. The permittivity in the CD cavity is known to be nearly the same as that of dioxane. The microenvironment around the reactant in the CD cavity is different from that in the reaction media. Three distinct microenvironmental effects are expected: a) microsolvent effects, b) the protection of unstable intermediates or products, and c) the solubilization of the reactant. In addition, conformational effects can also be expected: Molecular Encapsulation: Organic Reactions in Constrained SystemsEdited by Udo H. Brinker and Jean-Luc Mieusset

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Section: Additionmentioning

confidence: 99%

Reactions Mediated by Cyclodextrins

Takahashi

2010

Molecular Encapsulation

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“…Due to this special molecular arrangement, non-toxicity, water-solubility and commercial availability, b-CD is one of the most important and promising macromolecules and found numerous applications in pharmacy, drug delivery, separation processes, catalysis, food and industry [30]. There is evidence that metal ion can be complexed by cyclodextrins through hydroxyl groups, and this complex can be considered as metallo-enzyme model, and molecular recognition [31][32][33][34][35][36][37].…”

Section: Introductionmentioning

confidence: 99%

Nano-sized Mn3O4 and β-MnOOH from the decomposition of β-cyclodextrin–Mn: 1. Synthesis and characterization

Najafpour

Mostafalu

Kaboudin

2015

Journal of Photochemistry and Photobiology B: Biology

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“…One-pot threecomponent condensation of aldehydes, amines, and dimethylphosphite or trimethylphosphite is the most convenient method for the preparation of these compounds. In this context, some methods and catalysts have been reported such as LiClO 4 [8], oxalic acid [9], TaCl 5 -SiO 2 [10], β-cyclodextrin [11], Mg(ClO 4 ) 2 [12], InCl 3 [13], SmI 2 [14], amberlite-IR 120 [15], H 3 PW 12 O 40 [16], ionic liquid [17], FeCl 3 [18], and silica sulfuric acid [19]. However, these methodologies show varying degrees of success as well as limitations due to use of toxic organic solvents, expensive catalyst, prolonged reaction times, the requirement of special apparatus, or harsh reaction conditions.…”

Section: Introductionmentioning

confidence: 99%