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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: In this article, an anti-and enantioselective synthesis of β-amino aldehydes having an aliphatic substituent at the β-position was achieved by a combination of two catalytic reactions, that is, an initial Ni(II) complex-catalyzed isomerization of a double bond followed by a chiral phosphoric acid catalyzed aza-Petasis−Ferrier rearrangement, using hemiaminal allyl ethers as the initial substrate.
Abstract: Highly anti- and enantioselective synthesis of β-amino aldehydes having an aliphatic substituent at the β-position was accomplished by a combination of two catalytic reactions, that is, an initial Ni(II) complex-catalyzed isomerization of a double bond followed by a chiral phosphoric acid catalyzed aza-Petasis−Ferrier rearrangement, using hemiaminal allyl ethers as the initial substrate. The chiral phosphoric acid also functioned as an efficient resolving catalyst of racemic hemiaminal vinyl ethers.
TL;DR: In this paper, various glycals underwent smooth Lewis acid-catalysed allylic rearrangement reactions with O-nucleophiles to yield 2,3-unsaturated glycoside derivatives.
Abstract: Various glycals underwent smooth Lewis acid-catalysed allylic rearrangement reactions with O-nucleophiles to yield 2,3-unsaturated glycoside derivatives. In the hexose series predominantly α-D-, and in the pentose series β-D-anomers resulted. Among others Ω-cyano- as well as Ω-benzyloxycarbonylamino functionalised alcohols could be used successfully. With diols the corresponding 1,1′-bridged disaccharides could be obtained. 1. Dedicated to the memory of Prof. Akira Hasegawa.
TL;DR: The Ferrier rearrangement of a galactal derivative bearing trichloroacetimidate functionality as a leaving group at the C-3 position was performed in the presence of trimethylsilyl triflate as catalyst as mentioned in this paper.
Abstract: The Ferrier rearrangement of a galactal derivative 2 bearing the trichloroacetimidate functionality as a leaving group at the C-3 position was performed in the presence of trimethylsilyl triflate as catalyst; the corresponding pseudogalactal glycosides were obtained in excellent yield and stereoselectivity with a wide range of acceptors.
TL;DR: Exo -Glycosyl carbonates were shown to be efficient donors in microwave-assisted glycosylation and α-glycosyl additions occurred with excellent stereoselectivity and were complete in 4-8min with 75-92% yield as discussed by the authors.
Abstract: exo -Glycosyl carbonates were shown to be efficient glycosyl donors in microwave-assisted glycosylation. In these reactions α-glycosyl additions occurred with excellent stereoselectivity and were complete in 4–8 min with 75–92% yield. Interestingly exo -glycals were found to have higher activity than endo -glycals and common glycosides, the reactions of which can be improved by the addition of Lewis acid to result in a higher yield and enhanced stereoselectivity.
TL;DR: In this paper, a few bicyclic hybrid sugar molecules comprising of oxa-aza, oxaoxa, and oxa carbasugar fused skeletons were designed and synthesized from C-2 acetoxyglucal involving Ferrier rearrangement, Grignard addition, and ring-closing metathesis as key steps.
Abstract: A few bicyclic hybrid sugar molecules comprising of oxa-aza, oxa-oxa, and oxa-carbasugar fused skeletons were designed and synthesized from C-2 acetoxyglucal involving Ferrier rearrangement, Grignard addition, and ring-closing metathesis as key steps. The inhibitory activities of the synthesized molecules were tested against commercially available enzymes, which revealed the sugar–piperidine and sugar–pyran hybrids as potent and selective inhibitors.