Iodine-catalyzed Ferrier Reaction 1. A Mild and Highly Versatile Glycosylation of Hydroxyl and Phenolic Groups1

Occurrence, Biological Activities and Synthesis of Kaurane Diterpenes and their Glycosides

“…The synthesis of 2,3-dideoxyglycosides involves the mechanism known as "Ferrier rearrangement", which takes place by the treatment of a glycal with a reactive alcohol, in the presence of a Lewis acid, such as iodo [148], indium chloride [149], cerium chloride [150] or scandium triflate [151], leading to glycosides with an unsaturation between the carbons 2-3 of the glycopyranose ring. This and other glycosidation methods, not commented here in greater depth, are satisfactorily dealt with in specific bibliographical references in the area of carbohydrates chemistry [145,152,153].…”

Preparation of Sugar Amino Acids by Claisen‐Johnson Rearrangement: Synthesis and Incorporation into Enkephalin Analogues

“…Two methods were compared to perform the transformation, employing either I 2 [20] or FeCl 3 [21] as catalysts. Although similar high yields (81% with I 2 , 91% with FeCl 3 ) and identical anomeric ratios of the glycosides 2α and 2β (α/β ratio ϭ 8:1) were obtained with both methods, it was easier to purify the resulting product when FeCl 3 was used.…”

Kinetically controlled Ferrier rearrangement of 3-O-mesyl-d-glycal derivatives

“…1b Even under kinetic control, C-glycosidation is typical, 2 and a anomers predominate over b anomers. If I 2, 3 DDQ, 4 or iodonium dicolline perchlorate (IDCP) 5 are used as the catalyst, the reaction is thought to be mildly acidic or nonacidic, and the a anomer again becomes the major product. Without catalyst, for example, reaction of 1 with methanol gave the a anomer as the major product, 6 probably as a result of anomerization due to the acetic acid generated during the reaction.…”