Room-Temperature Ionic Liquids in Glycoscience: Opportunities and Challenges+

: Carbohydrates are fascinating molecular scaffolds known for their diverse applications in chemistry, biology, medicine, technology, and materials science. In addition, owing to the notable features of room-temperature ionic liquids (RTILs) such as high yield, short reaction time, simple handling, excellent recyclability, and environmentally benign nature, they have been extensively utilized as green solvents, catalysts, or both in a wide range of organic transformation methodologies for easy access of a diverse range of biologically relevant molecules. This review highlights the importance of RTILs that offer promising solutions in glycoscience, particularly in relevance to the dissolution, functionalization, glycosylation, and modification of carbohydrates as well as their challenges, impact, and future perspectives.

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Cholinium-amino acid based ionic liquids: a new method of synthesis and physico-chemical characterization

Physical Chemistry Chemical Physics ◽

10.1039/c5cp01612f ◽

2015 ◽

Vol 17 (32) ◽

pp. 20687-20698 ◽

Cited By ~ 80

Author(s):

Serena De Santis ◽

Giancarlo Masci ◽

Francesco Casciotta ◽

Ruggero Caminiti ◽

Eleonora Scarpellini ◽

...

Keyword(s):

Ionic Liquids ◽

Amino Acid ◽

Room Temperature ◽

Chemical Characterization ◽

New Method ◽

Room Temperature Ionic Liquids ◽

Synthetic Method ◽

Chemical Structures ◽

Physico Chemical ◽

Wide Range

Fourteen cholinium-amino acid based room temperature ionic liquids were prepared using a cleaner synthetic method. Chemicophysical properties were well correlated with the wide range of amino acid chemical structures.

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Ruthenium- and Rhodium-catalyzed Carbenoid Reactions of Diazoesters in Hexaalkylguanidinium-based Ionic Liquids

Zeitschrift für Naturforschung B ◽

10.1515/znb-2012-0408 ◽

2012 ◽

Vol 67 (4) ◽

pp. 347-353 ◽

Cited By ~ 2

Author(s):

Torsten Large ◽

Tobias Müller ◽

Helene Kunkel ◽

Stefan Buck ◽

Gerhard Maas

Keyword(s):

Ionic Liquid ◽

Ionic Liquids ◽

Room Temperature ◽

Reaction Medium ◽

High Yield ◽

Room Temperature Ionic Liquids ◽

Tert Butyl ◽

Trans Isomerization ◽

Intermolecular Reaction

Hexaalkylguanidinium-based room-temperature ionic liquids were investigated as solvents for the cyclopropanation of styrene with diazoacetates catalyzed by Rh2(OAc)4 or [Ru2(μ-OAc)2(CO)4]n. While the yields of the formed cyclopropanes are much lower compared to the reactions performed in dichloromethane, the diastereomeric ratio is not significantly affected by the change of the reaction medium. Immobilization of the catalysts is only partially successful. In contrast to this intermolecular reaction, the Ru-catalyzed formation of a β -lactam by an intramolecular carbenoid C-H insertion of an α-methoxycarbonyl-α-diazoacetamide occurs in high yield, similar to the Rh2(OAc)4-catalyzed reaction. The cis → trans isomerization of the resulting 1-tert-butyl-3-methoxycarbonyl-4-phenylazetidin- 2-one is accelerated in the ionic liquid N,N-dibutyl-N’ ,N’-diethyl-N’,N’-dihexylguanidinium triflate.

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