Organic reactions using water as solvent are reviewed with a focus on pericyclic reactions, carbonyl additions, stoichiometric organometallic reactions, oxidations and reductions which show an unusual outcome in terms of reactivity and selectivity compared with those performed in organic solvent. The advantages of using water as a solvent are discussed and related to the hydrophobic effects and the hydrogen-bonding ability of water with a special emphasis on its very high cohesive energy density which strongly favors organic reactions having a negative activation volume.

Water as Solvent in Organic Synthesis

Organometallic reactions in aqueous media. Indium-mediated allylation of sulfonimines

https://pubs.rsc.org/en/content/articlepdf/2011/cc/c1cc12800k

Iridium-catalysed condensation of alcohols and amines as a method for aminosugar synthesis.

Glycobiology is the comprehensive biological investigation of carbohydrates. The study of the role and function of complex carbohydrates often requires the attachment of carbohydrates to surfaces, their tagging with fluorophores, or their conversion into natural or non-natural glycoconjugates, such as glycopeptides or glycolipids. Glycobiology and its "omics", glycomics, require easy and robust chemical methods for the construction of these glycoconjugates. This review gives an overview of the rapidly expanding field of chemical reactions that selectively convert unprotected carbohydrates into glycoconjugates through the anomeric position. The discussion is divided in terms of the anomeric bond type of the newly formed glycoconjugates, including O-, N-, S-, and C-glycosides.

Chemoselective reactions for the synthesis of glycoconjugates from unprotected carbohydrates

Tin-mediated additions of allylic bromides to aldehydes and aldoses leads to adduct with high diastereo- and diastereofacial selectivity in the presence of indium trichloride in water.

Isabelle Isaac

Papers

A new and direct access to glycono-1,4-lactones from glycopyranoses by regioselective oxidation and subsequent ring restriction