Please use this identifier to cite or link to this item:
Title: Nucleophilic Trapping of Alkoxy-Stabilized Oxyallyl Systems Generated from Inosose 2-O-Mesylates
Contributor(s): Stockton, Kieran (author); Glover, Stephen  (author)orcid ; Greatrex, Ben  (author)orcid 
Publication Date: 2015
Open Access: Yes
DOI: 10.1055/s-0034-1379490Open Access Link
Handle Link:
Abstract: Protected inosose 2-O-mesylates generate oxyallyl systems by elimination of the mesylate group after enolization. The reaction is promoted by weak bases such as triethylamine and azide, and the oxyallyl systems are then trapped by nucleophilic alcohols or azide. Computations using DFT/B3LYP confirm that the singlet planar oxyallyl is stabilized by the exocyclic alkoxy group.
Publication Type: Journal Article
Source of Publication: Synlett, 26(1), p. 111-115
Publisher: Georg Thieme Verlag
Place of Publication: Germany
ISSN: 1437-2096
Field of Research (FOR): 030503 Organic Chemical Synthesis
030502 Natural Products Chemistry
030505 Physical Organic Chemistry
Socio-Economic Objective (SEO): 970103 Expanding Knowledge in the Chemical Sciences
860803 Human Pharmaceutical Treatments (e.g. Antibiotics)
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
Statistics to Oct 2018: Visitors: 353
Views: 446
Downloads: 0
Appears in Collections:Journal Article
School of Rural Medicine
School of Science and Technology

Files in This Item:
2 files
File Description SizeFormat 
Show full item record


checked on Nov 30, 2018

Page view(s)

checked on Mar 3, 2019
Google Media

Google ScholarTM



Items in Research UNE are protected by copyright, with all rights reserved, unless otherwise indicated.