Topic
Ferrier carbocyclization
About: Ferrier carbocyclization is a research topic. Over the lifetime, 66 publications have been published within this topic receiving 947 citations.
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TL;DR: In this paper, a three-component coupling reaction of functionalized cyclohexenone (+)- 6 derived from d-glucose by way of Ferrier's carbocyclization reaction, with vinyl cuprate and 2-alkoxypropanal 7 effectively constructed the carbon framework of 3 in a highly stereoselective manner.
21 citations
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TL;DR: An iron-catalyzed tandem isomerization-intramolecular aldolization reaction was developed to prepare cyclohexenone derivatives bearing substituents on the double bond, and it has been applied in a short synthesis of 4-epi-gabosines A and B, from d-glucose.
17 citations
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TL;DR: Fe2(SO4)3···xH2O catalyzes the Ferrier reaction of per−O−acetylated/benzylated glycals with alcohols to give 2,3−unsaturated α−glycosides in a few minutes under microwave irradiation as mentioned in this paper.
17 citations
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TL;DR: In this paper, the combination of α-zirconium sulfophenylphosphonate-methanphosphoneate and lithium bromide change the regioselectivity of this process affording 2-deoxy sugars in good yields.
Abstract: Layered α-zirconium sulfophenylphosphonate-methanphosphonate is a solid acid catalyst that catalyzes Ferrier rearrangement from d-glycals and alcoholic nucleophiles under mild reaction conditions in short time and good yields. Notably, the combination of α-zirconium sulfophenylphosphonate-methanphosphonate and lithium bromide change the regioselectivity of this process affording 2-deoxy sugars in good yields.
16 citations
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TL;DR: NaHSO(4) supported on silica gel catalyses the Ferrier rearrangement reaction of 3,4,6-tri-O-acetyl-D-glucal with alcohols and thiols to give the corresponding 2,3-unsaturated glycosides in high anomeric selectivity and good to excellent yield in short reaction time.
16 citations