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  Direct experimental characterization of the Ferrier glycosyl cation in the gas phase

Greis, K., Kirschbaum, C., Leichnitz, S., Gewinner, S., Schöllkopf, W., von Helden, G., et al. (2020). Direct experimental characterization of the Ferrier glycosyl cation in the gas phase. Organic Letters, 22(22), 8916-8919. doi:10.1021/acs.orglett.0c03301.

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 Creators:
Greis, Kim, Author
Kirschbaum, Carla, Author
Leichnitz, Sabrina1, Author              
Gewinner, Sandy, Author
Schöllkopf, Wieland, Author
von Helden, Gert, Author
Meijer, Gerard, Author
Seeberger, Peter H.1, Author              
Pagel, Kevin, Author
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1Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863308              

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Free keywords: Ions, Chemical structure, Infrared light, Free radicals, Cations
 Abstract: The Ferrier rearrangement reaction is crucial for the synthesis of pharmaceuticals. Although its mechanism was described more than 50 years ago, the structure of the intermediate remains elusive. Two structures have been proposed for this Ferrier glycosyl cation: a 1,2-unsaturated cation that is resonance-stabilized within the pyranose ring or a cation that is stabilized by the anchimeric assistance of a neighboring acetyl group. Using a combination of gas-phase cryogenic infrared spectroscopy in helium nanodroplets and first-principles density functional theory, we provide the first direct structural characterization of Ferrier cations. The data show that both acetylated glucal and galactal lead to glycosyl cations of the dioxolenium type.

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Language(s): eng - English
 Dates: 2020-11-052020
 Publication Status: Published in print
 Pages: -
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 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/acs.orglett.0c03301
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Title: Organic Letters
  Other : Org. Lett.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 22 (22) Sequence Number: - Start / End Page: 8916 - 8919 Identifier: ISSN: 1523-7060