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

Watanabe, Yuhya; Itoh, Tsubasa; Sakakibara, Tohru

doi:10.1016/j.carres.2008.12.015

Cited by 14 publications

(2 citation statements)

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“…Sakakibara and co‐workers developed a related two‐step strategy for the preparation of 2,3‐unsaturated glycosides from glycals containing C‐3 hydroxy groups (e.g., 40 Scheme ), by conversion to its corresponding methanesulfonates (e.g., 41 ), followed by in situ glycosylation 42. Several alcohols such as methanol, propan‐2‐ol, and even tert ‐butanol furnished the corresponding allylic glycosides 42 in the absence of catalyst on heating at 40 °C.…”

Section: Promoters For the Rearrangement Of Glycalsmentioning

confidence: 99%

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Recent Developments in the Ferrier Rearrangement

et al. 2013

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Glycals (1,2‐unsaturated, cyclic carbohydrate derivatives) readily undergo (catalyzed) substitution reactions at C‐1 accompanied by allylic rearrangement. This reaction, currently named Ferrier rearrangement, or the Ferrier I reaction, has established itself as a useful synthetic tool for carbohydrate transformations. By means of this reaction, glycals can be converted into highly useful 2,3‐unsaturated glycosides. This review summarizes recent developments in the use of promoters for the Ferrier rearrangement of O‐, N‐, C‐ and S‐nucleophiles with glycals.

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Section: Promoters For the Rearrangement Of Glycalsmentioning

confidence: 99%

“…Autocatalyzed reactions of 3‐ O ‐mesyl glycals42 or glycal‐derived allyl epoxides217 have also been used in the Ferrier‐type synthesis of thioglycosides. ( S )‐Camphorsulfonic acid has been shown to catalyze the conversion of 2,4,6‐tri‐ O ‐acetyl‐ D ‐glucal into 2,3‐unsaturated thioglycosides 51.…”

Section: Other Nucleophiles In the Frmentioning

confidence: 99%