ChemInform Abstract: Ferric Chloride: A New and Very Efficient Catalyst for the Ferrier Glycosylation Reaction.

Abstract

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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.…”

Iron(III) chloride catalyzed glycosylation of peracylated sugars with allyl/alkynyl alcohols

“…15 In addition, iron chloride was successfully employed for the Ferrier rearrangement. 16 Whilst there are several published procedures [4][5][6][7][8][9][10][11][12] for the glycosylation reactions, many of these methods require the use of expensive reagents and have limitations in terms of yields, stereoselectivities, reaction temperature, the catalyst/reagents used and their quantitative amounts. Therefore, our aim was to find a method that utilized mild, relatively cheap reagents and flexible enough to allow the synthesis of glycosides.…”

Metal nitrates catalysed O-glucosylation using acetyl glucal in organic solvents and ionic liquids: A comparative investigation

“…Besides, the synthetic utility of the Ferrier rearrangement is not limited to the preparation of unsaturated O-glycosides, since the variation of nucleophiles can result in S-and C-glycosides. The catalysts commonly employed to effect the rearrangement are either Lewis acids, such as BF 3 ·Et 2 O [9], SnCl 4 [10], FeCl 3 [11], Sc(OTf) 3 [12], LiBF 4 [13,14], InCl 3 [15], Yb(OTf) 3 [16], montmorillonite K10 [17], BiCl 3 [18], InBr 3 [19], Dy(OTf) 3 [20], CeCl 3 ·7H 2 O [21], ZnCl 2 [22] and ZrCl 4 [23] or oxidizing agents, such as iodonium dicollidinium perchlorate [24], 2,3-dichloro-5,6-dicyano-1,4-quinone [25] and Ce(NH 4 ) 2 (NO 3 ) 6 [26,27]. Very recently, Et 2 Zn/Pd(OAc) 2 [28] and HClO 4 -SiO 2 [29] have been reported to effect Ferrier glycosylation.…”