Topic
Ferrier rearrangement
About: Ferrier rearrangement is a research topic. Over the lifetime, 321 publications have been published within this topic receiving 5524 citations.
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TL;DR: Alkyl 2,3-unsaturated glycopyranosides have been prepared by the Ferrier rearrangement of acetyl protected glycals catalyzed by HClO 4 -SiO 2 as discussed by the authors.
Abstract: Alkyl 2,3-unsaturated glycopyranosides have been prepared by the Ferrier rearrangement of acetyl protected glycals catalyzed by HClO 4 -SiO 2 . Operational simplicity, use of economically convenient catalyst, mild reaction conditions, high yields, short reaction times are the key features of this protocol.
68 citations
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TL;DR: In this paper, the stereoselective total synthesis of the title compound starting from D-glucose is described, and the key steps in this synthesis are Ferrier rearrangement to construct the optically active cyclohexenone (C-ring), and Pd-catalyzed intramolecular Heck reaction to build the phenanthridone skeleton.
68 citations
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TL;DR: In this paper, a novel glycal-based O-glycosylation reaction, in which the substrates are not only peracetyl glycals but also perbenzyl glucals to afford the corresponding 2,3-unsaturated-O-glucosides via Ferrier rearrangement, was developed.
66 citations
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TL;DR: O-Glycosidations of glycals 1, 8 and 9 with several alcohols by using a catalytic amount of 2,3-dichloro-5,6-dicyano-p-benzoquinone under neutral conditions proceeds smoothly to give the corresponding 2, 3-unsaturated glycosides in high yields.
Abstract: O-Glycosidations of glycals 1, 8 and 9 with several alcohols by using a catalytic amount of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) under neutral conditions proceeds smoothly to give the corresponding 2,3-unsaturated glycosides in high yields.
63 citations