Highly facile biomimetic regioselective ring opening of epoxides to halohydrins in the presence of β-cyclodextrin

Reddy, M. Arjun; Surendra, K.; Bhanumathi, N.; Rao, K. Rama

doi:10.1016/s0040-4020(02)00614-2

Cited by 63 publications

(19 citation statements)

References 24 publications

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“…It is known that β-cyclodextrin and substrate can form a host-guest complex in water [15,16]. This complexation depends on the size, shape and hydrophobicity of the guest molecule.…”

Section: Resultsmentioning

confidence: 99%

β-Cyclodextrin promoted oxidation of primary amines to nitriles in water

Shi

2009

Front. Chem. Eng. China

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A facile, efficient and substrate-selective oxidation of the primary amines with NaClO as oxidant catalyzed by β-cyclodextrin (β-CD) has been developed in water for the first time, and the behavior of β-cyclodextrin that catalyzed the primary amines to nitriles in water was investigated. It was found that the primary amines which could form host-guest complexes with β-cyclodextrin were oxidized to nitriles with excellent yields at ambient temperature. The results show that β-cyclodextrin worked not only as a solubilizing agent but also as a catalyst in these reactions.

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“…It is known that β-cyclodextrin and substrate can form a host-guest complex in water [15,16]. This complexation depends on the size, shape and hydrophobicity of the guest molecule.…”

Section: Resultsmentioning

confidence: 99%

β-Cyclodextrin promoted oxidation of primary amines to nitriles in water

Shi

2009

Front. Chem. Eng. China

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“…Bromide-mediated ringopening can also be executed using a combination of N-bromosuccinimide, triphenylphosphine and dimethylformamide [610]. Most nucleophilic of all, iodide readily attacks styrene oxide (421) to give the iodohydrin 551, and the use of b-cyclodextrin directs the addition to the less-substituted carbon, presumably due to steric hindrance caused by guest-host complexation [611]. In the realm of asymmetric synthesis cyclic meso-epoxides can be desymmetrized by chloride attack using silicon tetrachloride catalyzed by PINDOX [612].…”

Section: Oxiranes J93mentioning

confidence: 99%

Three‐Membered Heterocycles. Structure and Reactivity

Murphree

2011

Modern Heterocyclic Chemistry

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“…36 halohydrins has been carried out with hydrogen and lithium halides in the presence of β -CD. 37 The β -CD inclusion complexes of aryloxyepoxides with amines afforded aminoalcohols enantioselectively in the solid state. 38 When carried out in water as the reaction medium, nearly racemic aminoalcohols were produced.…”

Section: Ring Opening Reactionsmentioning

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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Highly facile biomimetic regioselective ring opening of epoxides to halohydrins in the presence of β-cyclodextrin

Cited by 63 publications

References 24 publications

β-Cyclodextrin promoted oxidation of primary amines to nitriles in water

β-Cyclodextrin promoted oxidation of primary amines to nitriles in water

Three‐Membered Heterocycles. Structure and Reactivity

Reactions Mediated by Cyclodextrins

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