A novel glycosidation of glycosyl fluoride using a designed ionic liquid and its effect on the stereoselectivity

Sasaki, Kaname; Matsumura, Shuichi; Toshima, Kazunobu

doi:10.1016/j.tetlet.2004.07.128

Cited by 61 publications

(27 citation statements)

References 20 publications

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“…CN functionalized ILs were also found to stabilize reaction intermediate in glycosidation reactions (C-O coupling) reactions [113] (Fig. 6).…”

Section: Ionic Liquid-coordinated Complexes For Better Immobilizationmentioning

confidence: 98%

Applications of functionalized ionic liquids

Zhao

Fei

et al. 2006

SCI CHINA SER B

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“…CN functionalized ILs were also found to stabilize reaction intermediate in glycosidation reactions (C-O coupling) reactions [113] (Fig. 6).…”

Section: Ionic Liquid-coordinated Complexes For Better Immobilizationmentioning

confidence: 98%

Applications of functionalized ionic liquids

Zhao

Fei

et al. 2006

SCI CHINA SER B

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“…Sasaki et al 238 performed glycosidations of glucopyranosyl fluoride and alcohols, using different ILs containing a Brønsted acid as the catalyst (Scheme 22). In addition to achieving high yields, high β-stereoselectivities were also obtained in both [HMIM][OTf] and [CN(CH 2 ) 3 -MIM][Tf 2 N].…”

Section: Applications Of Ether- and Hydroxyl-functionalized Ilsmentioning

confidence: 99%

Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

2012

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In recent years, the designer nature of ionic liquids (ILs) has driven their exploration and exploitation in countless fields among the physical and chemical sciences. A fair measure of the tremendous attention placed on these fluids has been attributed to their inherent designer nature. And yet, there are relatively few examples of reviews which emphasize this vital aspect in an exhaustive or meaningful way. In this critical review, we systematically survey the physicochemical properties of the collective library of ether- and alcohol-functionalized ILs, highlighting the impact of ionic structure on features such as viscosity, phase behavior/transitions, density, thermostability, electrochemical properties, and polarity (e.g., hydrophilicity, hydrogen bonding capability). In the latter portions of this review, we emphasize the attractive applications of these functionalized ILs across a range of disciplines, including their use as electrolytes or functional fluids for electrochemistry, extractions, biphasic systems, gas separations, carbon capture, carbohydrate dissolution (particularly, the (ligno)celluloses), polymer chemistry, antimicrobial and antielectrostatic agents, organic synthesis, biomolecular stabilization and activation, and nanoscience. Finally, this review discusses anion-functionalized ILs, including sulfur- and oxygen-functionalized analogs, as well as choline-based deep eutectic solvents (DESs), an emerging class of fluids which can be sensibly categorized as semi-molecular cousins to the IL. Finally, the toxicity and biodegradability of ether- and alcohol-functionalized ILs are discussed and cautiously evaluated in light of recent reports. By carefully summarizing literature examples on the properties and applications of oxy-functional designer ILs up till now, it is our intent that this review offer a barometer for gauging future advances in the field as well as a trigger to spur further contemplation of these seemingly inexhaustible and—relative to their potential—virtually untouched fluids. It is abundantly clear that these remarkable fluidic materials are here to stay, just as certain design rules are slowly beginning to emerge. However, in fairness, serendipity also still plays an undeniable role, highlighting the need for both expanded in silico studies and a beacon to attract bright, young researchers to the field.

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“…[25,26] One attractive feature of ILs that distinguishes them from typical organic solvents is the potential to tailor their physiochemical properties. [30] There are excellent examples in the literature detailing the use of ILs in glycosidation reactions as either a promoter in a typical organic solvent, such as dichloromethane (DCM) or acetonitrile, or as the sole reaction medium. [30] There are excellent examples in the literature detailing the use of ILs in glycosidation reactions as either a promoter in a typical organic solvent, such as dichloromethane (DCM) or acetonitrile, or as the sole reaction medium.…”

Section: Introductionmentioning

confidence: 99%